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Journal articles on the topic 'Alkyl-Alkyl couplings'

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Published: 14 December 2024

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1

Li, Yangyang, Yuqiang Li, Long Peng, Dong Wu, Lei Zhu, and Guoyin Yin. "Nickel-catalyzed migratory alkyl–alkyl cross-coupling reaction." Chemical Science 11, no. 38 (2020): 10461–64. http://dx.doi.org/10.1039/d0sc03217d.

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2

Saito, Bunnai, and Gregory C. Fu. "Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature." Journal of the American Chemical Society 129, no. 31 (August 2007): 9602–3. http://dx.doi.org/10.1021/ja074008l.

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3

Qin, Tian, Min Zhou, and Jet Tsien. "Unsymmetrical Heterocycle Cross-Couplings Enabled by Sulfur(IV) Reagents." Synlett 31, no. 20 (August 14, 2020): 1962–66. http://dx.doi.org/10.1055/s-0040-1706412.

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Whereas metal-mediated cross-couplings find broad applications in syntheses of medicines, agrochemicals, and natural products, these powerful transformations have limited utility for Lewis basic substrates (e.g., heteroarenes), wherein basic functionalities coordinate to the metal center, hindering product formation. In this context, we have developed a transition-metal-free cross-coupling reaction mediated by sulfur(IV). This method leverages the ability of simple alkyl sulfinyl(IV) chlorides to form bipyramidal sulfurane complexes to drive a pseudo ‘reductive elimination’ process from the hypervalent sulfur atom, thereby readily providing unsymmetrical biheteroarenes.1 Introduction2 Historical Sulfurane(IV)-Mediated Couplings3 Unsymmetrical Heterocycle Cross-Couplings4 Conclusion
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4

Saito, Bunnai, and Gregory C. Fu. "Enantioselective Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Homobenzylic Halides." Journal of the American Chemical Society 130, no. 21 (May 2008): 6694–95. http://dx.doi.org/10.1021/ja8013677.

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5

Kunze, Udo, and Rolf Tittmann. "Phosphinsubstituierte Chelatliganden, XXIII [1] Darstellung und NMR-Spektren von Alkyl-arylphosphinothioformamiden, R(Ph)PC(S)NHMe / Phosphine-Substituted Chelate Ligands, XXIII [1] Synthesis and NMR Spectra of Alkyl-arylphosphinothioformamides, R(Ph)PC(S)NHMe." Zeitschrift für Naturforschung B 42, no. 1 (January 1, 1987): 77–83. http://dx.doi.org/10.1515/znb-1987-0115.

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Abstract A series of alkyl-arylsubstituted N-methyl phosphinothioformamides, R(Ph)PC(S)NHMe (2 a-g), with varying bulkiness of the alkyl rest was synthesized from the racemic secondary phosphines 1a-g and methyl isothiocyanate. 1H and 13C NMR spectra of 2a−g reveal signal sets of diastereotopic nuclei due to the asymmetry of the molecule. The chemical shift and coupling constants were confirmed by simulation in case of 2b, c. The vicinal 31P−13C couplings of the menthyl and neomenthyl compounds 2f, g show an "anti-Karplus" behaviour (3J(gauche) > 3J(trans)) and allow the conformational assignment of the alicyclic group. The 31P chemical shifts of 2a−d give a linear correlation with the cone angle of the alkyl substituents quoted from literature.
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6

Plunkett, Shane, Corey H. Basch, Samantha O. Santana, and Mary P. Watson. "Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings." Journal of the American Chemical Society 141, no. 6 (January 25, 2019): 2257–62. http://dx.doi.org/10.1021/jacs.9b00111.

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7

Bernauer, Josef, Guojiao Wu, and Axel Jacobi von Wangelin. "Iron-catalysed allylation–hydrogenation sequences as masked alkyl–alkyl cross-couplings." RSC Advances 9, no. 54 (2019): 31217–23. http://dx.doi.org/10.1039/c9ra07604b.

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An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)2 or Fe(acac)2, Et2O, r.t.) to furnish various alkene and styrene derivatives.
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8

Achonduh, George T., Niloufar Hadei, Cory Valente, Stephanie Avola, Christopher J. O'Brien, and Michael G. Organ. "On the role of additives in alkyl–alkyl Negishi cross-couplings." Chemical Communications 46, no. 23 (2010): 4109. http://dx.doi.org/10.1039/c002759f.

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9

Baker, Kristen M., Diana Lucas Baca, Shane Plunkett, Mitchell E. Daneker, and Mary P. Watson. "Engaging Alkenes and Alkynes in Deaminative Alkyl–Alkyl and Alkyl–Vinyl Cross-Couplings of Alkylpyridinium Salts." Organic Letters 21, no. 23 (November 25, 2019): 9738–41. http://dx.doi.org/10.1021/acs.orglett.9b03899.

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10

Owston, Nathan A., and Gregory C. Fu. "Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins." Journal of the American Chemical Society 132, no. 34 (September 2010): 11908–9. http://dx.doi.org/10.1021/ja105924f.

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11

Cauley, Anthony N., Melda Sezen-Edmonds, Eric M. Simmons, and Cullen L. Cavallaro. "Increasing saturation: development of broadly applicable photocatalytic Csp2–Csp3 cross-couplings of alkyl trifluoroborates and (hetero)aryl bromides for array synthesis." Reaction Chemistry & Engineering 6, no. 9 (2021): 1666–76. http://dx.doi.org/10.1039/d1re00192b.

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HTE was used to systematically investigate the reaction of alkyl trifluoroborates and aryl bromides under photocatalytic conditions. General conditions were identified for coupling of activated primary, benzylic and secondary alkyl trifluoroborates.
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12

Xu, Meng-Yu, and Bin Xiao. "Germatranes and carbagermatranes: (hetero)aryl and alkyl coupling partners in Pd-catalyzed cross-coupling reactions." Chemical Communications 57, no. 89 (2021): 11764–75. http://dx.doi.org/10.1039/d1cc04373k.

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13

Branchaud, Bruce P., and William D. Detlefsen. "Cobaloxime-catalyzed radical alkyl-styryl cross couplings." Tetrahedron Letters 32, no. 44 (October 1991): 6273–76. http://dx.doi.org/10.1016/0040-4039(91)80145-v.

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14

Pound, Sarah M., and Mary P. Watson. "Asymmetric synthesis via stereospecific C–N and C–O bond activation of alkyl amine and alcohol derivatives." Chemical Communications 54, no. 87 (2018): 12286–301. http://dx.doi.org/10.1039/c8cc07093h.

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15

Bisz, Elwira, and Michal Szostak. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents." Molecules 25, no. 1 (January 6, 2020): 230. http://dx.doi.org/10.3390/molecules25010230.

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Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.
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16

Owston, Nathan A., and Gregory C. Fu. "ChemInform Abstract: Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins." ChemInform 42, no. 6 (January 13, 2011): no. http://dx.doi.org/10.1002/chin.201106074.

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17

Villanueva-Kasis, Oscar, Denisse A. de Loera, Sandra L. Castañón-Alonso, Armando Domínguez-Ortiz, Leticia Lomas-Romero, Ilich A. Ibarra, Eduardo González-Zamora, and Alejandro Islas-Jácome. "Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines." Proceedings 9, no. 1 (November 14, 2018): 34. http://dx.doi.org/10.3390/ecsoc-22-05769.

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Four new α-β-unsaturated alkyl-ester chiral amines were synthesized in excellent yields (77–95%) via peptide couplings from their corresponding α-β-unsaturated alkyl-ester anilines and N-Boc protected chiral aminoacids. To our delight, these polyfunctionalized compounds are being used as starting reagents in Ugi-type three-component reactions (Ugi-3CR) together with alkyl- and aryl-aldehydes and a chain-ring tautomerizable amino acid-containing isocyanide to synthesize novel oxazole-based macrocycle precursors. Thus, the aim of this communication is to show our most recent results of the synthesis and use of new and complex chiral amines to assemble macrocyclic polypeptides with potential application in medicinal chemistry, such as the post-surgical antibiotic Vancomycin.
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18

Penner, Glenn H. "Conformational preference and internal rotation about the C1—Cα bond in phenylacetaldehyde and some benzyl alkyl ketones from 1H nuclear magnetic resonance and abinitio molecular orbital calculations." Canadian Journal of Chemistry 65, no. 3 (March 1, 1987): 538–40. http://dx.doi.org/10.1139/v87-094.

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Analysis of the 1H nuclear magnetic resonance spectra of the benzyl moieties in phenylacetaldehyde, benzyl methyl ketone, benzyl ethyl ketone, benzyl isopropyl ketone, and 3,5-dichlorobenzyl tert-butyl ketone yields the long-range couplings between ring and α protons. These stereospecific couplings change very little upon replacement of the aldehydic hydrogen by various alkyl groups. The couplings for all the molecules studied fall within the ranges 4J(CH2, Ho) = −0.566 ± 0.008 Hz, 5J(CH2, Hm) = 0.278 ± 0.002 Hz, and 6J(CH2, Hp) = −0.409 ± 0.010 Hz, suggesting that in the ketones the alkyl group prefers to be trans to the phenyl ring and does not interfere with rotation about the C1—Cα bond. The long-range couplings are consistent with a potential function V(θ) = 8.4 ± 1.2 sin2 θ for two-fold rotation about the C1—Cα bond; θ is the angle between the carbonyl and benzene ring plane. Abinitio molecular orbital calculations on phenylacetaldehyde at the STO-3G level with the C=O bond cis to the phenyl group yield a potential of V(θ) = (8.65 ± 0.73) sin2 θ + (1.27 ± 0.80) sin2 2θ, rather close to the experimental potential but with a small fourfold component. The spin–spin coupling constant between the aldehydic and α protons displays a solvent dependence consistent with previously reported values. The insensitivity of 4J(CH2, Ho), 5J(CH2, Hm), and 6J(CH2, Hp) to solvent suggests that [Formula: see text] is very weakly dependent on the rotation of the aldehyde group.
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19

Crisp, GT, and S. Papadopoulos. "Palladium-Mediated Transformations of Heteroaromatic Triflates." Australian Journal of Chemistry 42, no. 2 (1989): 279. http://dx.doi.org/10.1071/ch9890279.

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Quinolyl triflates and isoquinolyl triflates undergo palladium-catalysed couplings with organostannanes, organoaluminiums and activated alkenes. The range of organic groups which can be transferred to the heteroaromatic substrate includes aryl, vinyl, alkynyl, alkyl and hydride.
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20

El-Maiss, Janwa, Tharwat Mohy El Dine, Chung-Shin Lu, Iyad Karamé, Ali Kanj, Kyriaki Polychronopoulou, and Janah Shaya. "Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings." Catalysts 10, no. 3 (March 5, 2020): 296. http://dx.doi.org/10.3390/catal10030296.

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Boron chemistry has evolved to become one of the most diverse and applied fields in organic synthesis and catalysis. Various valuable reactions such as hydroborylations and Suzuki–Miyaura cross-couplings (SMCs) are now considered as indispensable methods in the synthetic toolbox of researchers in academia and industry. The development of novel sterically- and electronically-demanding C(sp3)–Boron reagents and their subsequent metal-catalyzed cross-couplings attracts strong attention and serves in turn to expedite the wheel of innovative applications of otherwise challenging organic adducts in different fields. This review describes the significant progress in the utilization of classical and novel C(sp3)–B reagents (9-BBN and 9-MeO-9-BBN, trifluoroboronates, alkylboranes, alkylboronic acids, MIDA, etc.) as coupling partners in challenging metal-catalyzed C(sp3)–C(sp2) cross-coupling reactions, such as B-alkyl SMCs after 2001.
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21

BRANCHAUD, B. P., and W. D. DETLEFSEN. "ChemInform Abstract: Cobaloxime-Catalyzed Radical Alkyl-Styryl Cross Couplings." ChemInform 23, no. 26 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199226051.

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22

Davis, Mia, Mathias O. Senge, and Oliver B. Locos. "Anthracenylporphyrins." Zeitschrift für Naturforschung B 65, no. 12 (December 1, 2010): 1472–84. http://dx.doi.org/10.1515/znb-2010-1211.

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We report the synthesis and characterization of meso-anthracenylporphyrins with zinc and nickel metal centers. A variety of novel aryl and alkyl meso-substituted anthracenylporphyrins were synthesized via step-wise Suzuki cross-coupling reactions using anthracenyl boronates. This method was compared to standard syntheses based on condensation reactions to yield anthracenylporphyrins of the A2B2- and A3B-type. The work was complemented by the synthesis of a number of the functionalized anthracene derivatives via Suzuki couplings. Selected systems were subjected to single-crystal X-ray analysis which revealed an unusual close packing for nickel(II) anthracenylporphyrins.
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23

Parmar, Dixit, Lena Henkel, Josef Dib, and Magnus Rueping. "Iron catalysed cross-couplings of azetidines – application to the formal synthesis of a pharmacologically active molecule." Chemical Communications 51, no. 11 (2015): 2111–13. http://dx.doi.org/10.1039/c4cc09337b.

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A protocol for the cross-coupling of azetidines with aryl, heteroaryl, vinyl and alkyl Grignard reagents has been developed under iron catalysis. In addition, a short formal synthesis of a pharmacologically active molecule was demonstrated.
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24

Paul, Avishek, Mark D. Smith, and Aaron K. Vannucci. "Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl–Alkyl Cross-Couplings." Journal of Organic Chemistry 82, no. 4 (February 2, 2017): 1996–2003. http://dx.doi.org/10.1021/acs.joc.6b02830.

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25

Zhou, Jianrong (Steve), and Gregory C. Fu. "Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides." Journal of the American Chemical Society 125, no. 48 (December 2003): 14726–27. http://dx.doi.org/10.1021/ja0389366.

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26

Zhou, Jianrong (Steve), and Gregory C. Fu. "Suzuki Cross-Couplings of Unactivated Secondary Alkyl Bromides and Iodides." Journal of the American Chemical Society 126, no. 5 (February 2004): 1340–41. http://dx.doi.org/10.1021/ja039889k.

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27

Guérinot, Amandine, and Janine Cossy. "Cobalt-Catalyzed Cross-Couplings between Alkyl Halides and Grignard Reagents." Accounts of Chemical Research 53, no. 7 (July 10, 2020): 1351–63. http://dx.doi.org/10.1021/acs.accounts.0c00238.

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28

McMahon, Caitlin M., and Erik J. Alexanian. "Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides." Angewandte Chemie 126, no. 23 (April 24, 2014): 6084–87. http://dx.doi.org/10.1002/ange.201311323.

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29

McMahon, Caitlin M., and Erik J. Alexanian. "Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides." Angewandte Chemie International Edition 53, no. 23 (April 23, 2014): 5974–77. http://dx.doi.org/10.1002/anie.201311323.

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30

Ivanov, Mikhail Yu, Sergey A. Prikhod’ko, Olga D. Bakulina, Alexey S. Kiryutin, Nicolay Yu Adonin, and Matvey V. Fedin. "Validation of Structural Grounds for Anomalous Molecular Mobility in Ionic Liquid Glasses." Molecules 26, no. 19 (September 26, 2021): 5828. http://dx.doi.org/10.3390/molecules26195828.

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Ionic liquid (IL) glasses have recently drawn much interest as unusual media with unique physicochemical properties. In particular, anomalous suppression of molecular mobility in imidazolium IL glasses vs. increasing temperature was evidenced by pulse Electron Paramagnetic Resonance (EPR) spectroscopy. Although such behavior has been proven to originate from dynamics of alkyl chains of IL cations, the role of electron spin relaxation induced by surrounding protons still remains unclear. In this work we synthesized two deuterated imidazolium-based ILs to reduce electron–nuclear couplings between radical probe and alkyl chains of IL, and investigated molecular mobility in these glasses. The obtained trends were found closely similar for deuterated and protonated analogs, thus excluding the relaxation-induced artifacts and reliably demonstrating structural grounds of the observed anomalies in heterogeneous IL glasses.
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31

Wang, Nai-Xing, Yalan Xing, Lei-Yang Zhang, and Yue-Hua Wu. "C(sp3)–H Bond Functionalization of Alcohols, Ketones, Nitriles, Ethers and Amides using tert-Butyl Hydroperoxide as a Radical Initiator." Synlett 32, no. 01 (July 31, 2020): 23–29. http://dx.doi.org/10.1055/s-0040-1706406.

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The C(sp3)–H bond is found widely in organic molecules. Recently, the functionalization of C(sp3)–H bonds has developed into a powerful tool for augmenting highly functionalized frameworks in organic synthesis. Based on the results obtained in our group, the present account mainly summarizes recent progress on the functionalization of C(sp3)–H bonds of aliphatic alcohols, ketones, alkyl nitriles, and ethers with styrene or cinnamic acid using tert-butyl hydroperoxide (TBHP) as a radical initiator.1 Introduction2 Oxidative Coupling of Styrenes with C(sp3)–H Bonds3 Decarboxylative Cross-Couplings of α,β-Unsaturated Carboxylic Acids with C(sp3)–H Bonds4 Conclusions
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32

Powell, David A., Toshihide Maki, and Gregory C. Fu. "Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents." Journal of the American Chemical Society 127, no. 2 (January 2005): 510–11. http://dx.doi.org/10.1021/ja0436300.

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33

O’Neil, Gregory W., and Alois Fürstner. "B-Alkyl Suzuki couplings for the stereoselective synthesis of substituted pyrans." Chemical Communications, no. 36 (2008): 4294. http://dx.doi.org/10.1039/b806898d.

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34

Malhotra, Sushant, Pamela S. Seng, Stefan G. Koenig, Alan J. Deese, and Kevin A. Ford. "Chemoselective sp2-sp3 Cross-Couplings: Iron-Catalyzed Alkyl Transfer to Dihaloaromatics." Organic Letters 15, no. 14 (July 5, 2013): 3698–701. http://dx.doi.org/10.1021/ol401508u.

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35

Eckhardt, Matthias, and Gregory C. Fu. "The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides." Journal of the American Chemical Society 125, no. 45 (November 2003): 13642–43. http://dx.doi.org/10.1021/ja038177r.

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36

Sedláček, Ondřej, Petra Břehová, Radek Pohl, Antonín Holý, and Zlatko Janeba. "The synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) derivatives by diverse cross-coupling reactions." Canadian Journal of Chemistry 89, no. 4 (April 2011): 488–98. http://dx.doi.org/10.1139/v11-001.

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Diisopropyl 8-bromo-2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine was used as a starting material for the synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) analogues. A systematic screening of diverse cross-coupling reactions was carried out. Stille, Suzuki–Miyaura, Negishi, and Sonogashira cross-couplings, as well as Pd-catalysed reactions with trialkylaluminiums, were employed for the introduction of various alkyl, alkenyl, alkynyl, aryl, and hetaryl substituents to the C-8 position of the 2,6-diaminopurine moiety. In contrast to the potent parent compound PMEDAP, which exhibits potent antiretroviral and antitumor activity, none of the sixteen newly synthesized 8-C-substituted analogues of PMEDAP showed any specific antiviral activity.
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37

Cornella, Josep, and Matthew O’Neill. "Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles." Synthesis 50, no. 20 (September 10, 2018): 3974–96. http://dx.doi.org/10.1055/s-0037-1609941.

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While the advent of transition-metal catalysis has undoubtedly transformed synthetic chemistry, problems persist with the introduction of secondary and tertiary alkyl nucleophiles into C(sp2) aryl electrophiles. Complications arise from the delicate organometallic intermediates typically invoked by such processes, from which competition between the desired reductive elimination event and the deleterious β-H elimination pathways can lead to undesired isomerization of the incoming nucleophile. Several methods have integrated distinct combinations of metal, ligand, nucleophile, and electrophile to provide solutions to this problem. Despite substantial progress, refinements to current protocols will facilitate the realization of complement reactivity and improved functional group tolerance. These issues have become more pronounced in the context of green chemistry and sustainable catalysis, as well as by the current necessity to develop robust, reliable cross-couplings beyond less explored C(sp2)–C(sp2) constructs. Indeed, the methods discussed herein and the elaborations thereof enable an ‘unlocking’ of accessible topologically enriched chemical space, which is envisioned to influence various domains of application.1 Introduction2 Mechanistic Considerations3 Magnesium Nucleophiles4 Zinc Nucleophiles5 Boron Nucleophiles6 Other Nucleophiles7 Tertiary Nucleophiles8 Reductive Cross-Coupling with in situ Organometallic Formation9 Conclusion
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38

Taratayko, Andrey I., Yurii I. Glazachev, Ilia V. Eltsov, Elena I. Chernyak, and Igor A. Kirilyuk. "3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains." Molecules 27, no. 6 (March 16, 2022): 1922. http://dx.doi.org/10.3390/molecules27061922.

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Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N–O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2-tert-butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2-tert-butyl-1-pyrroline-1-oxides via either the addition of ethinylmagnesium bromide with subsequent hydrogenation or via treatment with ethyllithium. The new nitroxides showed excellent stability to reduction with ascorbate with no evidence for additional large hyperfine couplings in the EPR spectra.
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39

Liu, Lei, Maria Camila Aguilera, Wes Lee, Cassandra R. Youshaw, Michael L. Neidig, and Osvaldo Gutierrez. "General method for iron-catalyzed multicomponent radical cascades–cross-couplings." Science 374, no. 6566 (October 22, 2021): 432–39. http://dx.doi.org/10.1126/science.abj6005.

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Iron links a trio Iron holds particular appeal as a catalytic metal—it is safe and abundant, as well as a mainstay of enzymatic reactivity. Nonetheless, in synthetic construction of carbon-carbon bonds, modern chemists have largely had to rely on rarer metals such as palladium. Liu et al . now report that coordination of iron by a bulky chelating phosphine ligand enables efficient mutual coupling of three different reactants—an alkyl halide, an aryl Grignard, and an olefin—to form two carbon-carbon bonds (see the Perspective by Lefèvre). A combination of Mössbauer spectroscopy, crystallography, and computational simulations illuminates the mechanism. —JSY
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40

Wilsily, Ashraf, Francesco Tramutola, Nathan A. Owston, and Gregory C. Fu. "New Directing Groups for Metal-Catalyzed Asymmetric Carbon–Carbon Bond-Forming Processes: Stereoconvergent Alkyl–Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles." Journal of the American Chemical Society 134, no. 13 (March 26, 2012): 5794–97. http://dx.doi.org/10.1021/ja301612y.

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41

Luo, Yongrui, Yuli Li, Jian Wu, Xiao-Song Xue, John F. Hartwig, and Qilong Shen. "Oxidative addition of an alkyl halide to form a stable Cu(III) product." Science 381, no. 6662 (September 8, 2023): 1072–79. http://dx.doi.org/10.1126/science.adg9232.

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The step that cleaves the carbon-halogen bond in copper-catalyzed cross-coupling reactions remains ill defined because of the multiple redox manifolds available to copper and the instability of the high-valent copper product formed. We report the oxidative addition of α-haloacetonitrile to ionic and neutral copper(I) complexes to form previously elusive but here fully characterized copper(III) complexes. The stability of these complexes stems from the strong Cu−CF 3 bond and the high barrier for C( CF 3 )−C( CH 2 CN ) bond-forming reductive elimination. The mechanistic studies we performed suggest that oxidative addition to ionic and neutral copper(I) complexes proceeds by means of two different pathways: an S N 2-type substitution to the ionic complex and a halogen-atom transfer to the neutral complex. We observed a pronounced ligand acceleration of the oxidative addition, which correlates with that observed in the copper-catalyzed couplings of azoles, amines, or alkynes with alkyl electrophiles.
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42

Lee, Nicholas R., Roscoe T. H. Linstadt, Danielle J. Gloisten, Fabrice Gallou, and Bruce H. Lipshutz. "B-Alkyl sp3–sp2 Suzuki–Miyaura Couplings under Mild Aqueous Micellar Conditions." Organic Letters 20, no. 10 (May 8, 2018): 2902–5. http://dx.doi.org/10.1021/acs.orglett.8b00961.

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43

Powell, David A., and Gregory C. Fu. "Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl Bromides." Journal of the American Chemical Society 126, no. 25 (June 2004): 7788–89. http://dx.doi.org/10.1021/ja047433c.

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44

Lee, Jae-Young, and Gregory C. Fu. "Room-Temperature Hiyama Cross-Couplings of Arylsilanes with Alkyl Bromides and Iodides." Journal of the American Chemical Society 125, no. 19 (May 2003): 5616–17. http://dx.doi.org/10.1021/ja0349352.

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45

Schwarzwalder, Gregg M., Carson D. Matier, and Gregory C. Fu. "Enantioconvergent Cross‐Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes." Angewandte Chemie 131, no. 11 (March 11, 2019): 3609–12. http://dx.doi.org/10.1002/ange.201814208.

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46

Malhotra, Sushant, Pamela S. Seng, Stefan G. Koenig, Alan J. Deese, and Kevin A. Ford. "ChemInform Abstract: Chemoselective sp2-sp3Cross-Couplings: Iron-Catalyzed Alkyl Transfer to Dihaloaromatics." ChemInform 44, no. 50 (November 21, 2013): no. http://dx.doi.org/10.1002/chin.201350171.

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47

Schwarzwalder, Gregg M., Carson D. Matier, and Gregory C. Fu. "Enantioconvergent Cross‐Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes." Angewandte Chemie International Edition 58, no. 11 (March 11, 2019): 3571–74. http://dx.doi.org/10.1002/anie.201814208.

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48

McMahon, Caitlin M., and Erik J. Alexanian. "ChemInform Abstract: Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides." ChemInform 45, no. 48 (November 13, 2014): no. http://dx.doi.org/10.1002/chin.201448061.

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49

Liang, Yufan, and Gregory C. Fu. "Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent." Angewandte Chemie International Edition 54, no. 31 (June 12, 2015): 9047–51. http://dx.doi.org/10.1002/anie.201503297.

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50

Liang, Yufan, and Gregory C. Fu. "Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent." Angewandte Chemie 127, no. 31 (June 12, 2015): 9175–79. http://dx.doi.org/10.1002/ange.201503297.

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