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Journal articles on the topic 'Heck-type reaction'

Author: Grafiati

Published: 6 September 2023

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1

Kurandina, Daria, Padon Chuentragool, and Vladimir Gevorgyan. "Transition-Metal-Catalyzed Alkyl Heck-Type Reactions." Synthesis 51, no. 05 (February 7, 2019): 985–1005. http://dx.doi.org/10.1055/s-0037-1611659.

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The Heck reaction is one of the most reliable and useful strategies for the construction of C–C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.1 Introduction2 Pd-Catalyzed Heck-Type Reactions2.1 Benzylic Electrophiles2.2 α-Carbonyl Alkyl Halides2.3 Fluoroalkyl Halides2.4 α-Functionalized Alkyl Halides2.5 Unactivated Alkyl Electrophiles3 Ni-Catalyzed Heck-Type Reactions3.1 Benzylic Electrophiles3.2 α-Carbonyl Alkyl Halides3.3 Unactivated Alkyl Halides4 Co-Catalyzed Heck-Type Reactions5 Cu-Catalyzed Heck-Type Reactions6 Other Metals in Heck-Type Reactions7 Conclusion

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2

Zhou, Huan, Liang Ge, Jinshuai Song, Wujun Jian, Yajun Li, Chunsen Li, and Hongli Bao. "HOTf-Catalyzed Alkyl-Heck-type Reaction." iScience 3 (May 2018): 255–63. http://dx.doi.org/10.1016/j.isci.2018.04.020.

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3

Lee, A. L. "Enantioselective oxidative boron Heck reactions." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5357–66. http://dx.doi.org/10.1039/c5ob01984b.

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4

Wang, Sa-Sa, and Guo-Yu Yang. "Recent developments in low-cost TM-catalyzed Heck-type reactions (TM = transition metal, Ni, Co, Cu, and Fe)." Catalysis Science & Technology 6, no. 9 (2016): 2862–76. http://dx.doi.org/10.1039/c5cy02235e.

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5

Newman, Stephen, and Jaya Vandavasi. "A High-Throughput Approach to Discovery: Heck-Type Reactivity with Aldehydes." Synlett 29, no. 16 (June 12, 2018): 2081–86. http://dx.doi.org/10.1055/s-0037-1610161.

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The classical Heck reaction is among the most powerful methods available for the construction of C–C bonds. Modification of this transformation to utilize diverse organohalide coupling partners has resulted in new reactions such as the silyl-Heck, aza-Heck, and boryl-Heck reactions. In contrast, modification of the olefin coupling partner is rare. For instance, use of the π-bond of an aldehyde instead of an alkene would provide ketones via a carbonyl-Heck process. This seemingly minor manipulation of the Heck reaction has proven surprisingly difficult to realize in practice. Through the use of high-throughput experimentation techniques, an efficient catalyst system for this transformation was identified, enabling the intermolecular coupling of organotriflates and aldehydes to synthesize diverse ketones.

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6

Zhu, Xiaoyan, Feng Liu, Xinwu Ba, and Yonggang Wu. "Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer." Polymers 15, no. 16 (August 10, 2023): 3360. http://dx.doi.org/10.3390/polym15163360.

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The synthesis of ladder-type 9,9′-bifluorenylidene-based conjugated polymer is reported. Unlike the typical synthetic strategy, the new designed ladder-type conjugated polymer is achieved via tandem Suzuki polymerization/Heck cyclization reaction in one-pot. In the preparation process, Suzuki polymerization reaction occurred first and then the intramolecular Heck cyclization followed smoothly under the same catalyst Pd(PPh3)4. The model reaction proved that the introduction of iodine (I) for this tandem reaction can effectively control the sequential bond-forming process and inhibit the additional competitive side reactions. Thus, small-molecule model compounds could be obtained in high yields. The successes of the synthesized small molecule and polymer compounds indicate that the Pd-catalyzed tandem reaction may be an effective strategy for improving extended π-conjugated materials.

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7

Helaja, Juho, and Richard Göttlich. "A new catalytic hetero-Heck type reaction." Chemical Communications, no. 7 (March 6, 2002): 720–21. http://dx.doi.org/10.1039/b201209j.

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8

Pirisedigh, Azadeh, Amin Zarei, Hojjat Seyedjamali, Leila Khazdooz, and Abdol R. Hajipour. "Heck-type reaction of aryldiazonium silica sulfates." Monatshefte für Chemie - Chemical Monthly 143, no. 5 (September 23, 2011): 791–95. http://dx.doi.org/10.1007/s00706-011-0632-1.

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9

Kitamura, Tsugio, and Yuzo Fujiwara. "ChemInform Abstract: Dehydrogenative Heck-Type Reactions: The Fujiwara-Moritani Reaction." ChemInform 46, no. 15 (March 26, 2015): no. http://dx.doi.org/10.1002/chin.201515342.

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10

Teng, Shenghan, Malcolm E. Tessensohn, Richard D. Webster, and Jianrong Steve Zhou. "Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides." ACS Catalysis 8, no. 8 (July 2, 2018): 7439–44. http://dx.doi.org/10.1021/acscatal.8b02029.

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11

KURIHARA, Yuji, Mikiko SODEOKA, and Masakatsu SHIBASAKI. "Asymmetric Heck-Type Reaction Utilizing Hypervalent Alkenyliodonium Salt." CHEMICAL & PHARMACEUTICAL BULLETIN 42, no. 11 (1994): 2357–59. http://dx.doi.org/10.1248/cpb.42.2357.

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12

Shults, E. E. "Modification of Biologically Active Plant Metabolites Via the Transition Metal Catalyzed Reactions." Eurasian Chemico-Technological Journal 15, no. 3 (May 13, 2013): 175. http://dx.doi.org/10.18321/ectj221.

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Developed by the author’s research laboratory methods of functionalization of some plant metabolites or their derivatives, viz., the eudesmane-type methylenelactones, diterpene and morphinane alkaloids, furanolabdanoids, and coumarins, using the transition metal catalyzed reactions, are reviewed. The activity<br />of linear methylene lactone of the eudesmane type in the Heck reaction are analyzed. It is shown that the outcome of the Heck reaction is significantly influenced by the structure of methylidenelactone. The Pd-catalyzed arylation of isoalantolactone with arylhalogenides or 6-bromodeoxyvasicinone occurred with<br />formation mainly of cross-coupling products with the (E) - configuration of the double bond. Synthesis of halogen derivatives of lappaconitine, tetrahydrothebaine and dihydrothebaine-hydroquinone and investigation of in the Heck or Sonogashira reactions gave the possibility for obtaining of new alkaloid derivatives with additional substituents in the aromatic rings. Homocoupling reaction or Sonogashira crosscoupling reaction of 5´- ethynyllappaconitine are used for synthesis of dimeric alkaloids of aconitane types. Pd-catalyzed amination of 2-(1,3-dibromoprop-2-ylidene)oreoselone and the transformations of oreoselone triflate, upon the action of palladium compounds allowed us to accomplish new modifications of linear furocoumarins. The method of enyne cycloisomerization of <em>ω</em>-alkynylfurans catalyzed with Au(III) was successfully obtained in the transformations of furanolabdanoids. The copper(I) salts catalyzed 1,3-dipolar cycloaddition reaction of azides to terminal alkynes belongs to the group of click-reactions was used in the synthesis of macrocyclic structures of labdane diterpenoids. The copper-catalyzed 1,3-dipolar cycloaddition reaction of 2 - azidooreoselone with various alkynes yielded diverse 2-(1,2,3-triazolyl)furocoumarins. The advantages of transition metal catalyzed reactions to the transformations of plant metabolites and its derivatives shown the possibility of introduction of several bioisosteric groups, and other fragments providing additional interactions and selectivity of binding with receptors and enzymes.

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13

Hu, Fangdong, Ying Xia, Zhenxing Liu, Chen Ma, Yan Zhang, and Jianbo Wang. "Palladium-catalyzed three-component reaction of N-tosylhydrazone, norbornene and aryl halide." Org. Biomol. Chem. 12, no. 22 (2014): 3590–93. http://dx.doi.org/10.1039/c4ob00590b.

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14

Li, Lixin, Zhengguang Zhao, Jing Xu, Haotian Luo, Yong Li, Xiantao Ma, Lin Tang, Bo Ren, Xinhua Cao, and Yan-Na Ma. "Synthesis of remote fluoroalkylated alkenes by a palladium-catalyzed relay Heck-type reaction." Chemical Communications 56, no. 65 (2020): 9384–87. http://dx.doi.org/10.1039/c9cc10048b.

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15

Fan, Tao, Wei-Dong Meng, and Xingang Zhang. "Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides." Beilstein Journal of Organic Chemistry 13 (December 6, 2017): 2610–16. http://dx.doi.org/10.3762/bjoc.13.258.

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An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction.

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16

Ojha, Subhadra, and Niranjan Panda. "Pd-Catalyzed desulfitative arylation of olefins by N-methoxysulfonamide." Organic & Biomolecular Chemistry 20, no. 6 (2022): 1292–98. http://dx.doi.org/10.1039/d1ob02360h.

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17

Xu, Ren-Rui, Wei Wang, Xinxin Qi, and Xiao-Feng Wu. "Palladium-catalyzed cascade Heck-type thiocarbonylation for the synthesis of functionalized thioesters." Organic Chemistry Frontiers 9, no. 5 (2022): 1417–21. http://dx.doi.org/10.1039/d2qo00096b.

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18

Mao, Jiangang, Shuo-Qing Zhang, Bing-Feng Shi, and Weiliang Bao. "Palladium(0)-catalyzed cyclopropanation of benzyl bromides via C(sp3)–H bond activation." Chem. Commun. 50, no. 28 (2014): 3692–94. http://dx.doi.org/10.1039/c3cc49231a.

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19

Dou, Yingchao, Liting Yang, Lu Zhang, Panke Zhang, Heng Li, and Guanyu Yang. "Palladium-catalyzed reductive Heck-type vinylative dearomatization of unfunctionalized halonaphthalene derivatives." RSC Advances 6, no. 102 (2016): 100632–35. http://dx.doi.org/10.1039/c6ra22310a.

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20

Cheng, Jiang, Zhishi Ye, Fan Chen, Fang Luo, Wenhui Wang, Baoda Lin, and Xiaofei Jia. "Palladium-Catalyzed Mizoroki-Heck-Type Reaction of Aryl Trimethoxysilanes." Synlett 2009, no. 13 (July 16, 2009): 2198–200. http://dx.doi.org/10.1055/s-0029-1217571.

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21

Yamashita, Hiroshi, Toshi-aki Kobayashi, Teruyuki Hayashi, and Masato Tanaka. "Heck-type Reaction of lodotrimethylsilane with Olefins Affording Alkenyltrimethylsilanes." Chemistry Letters 20, no. 5 (May 1991): 761–62. http://dx.doi.org/10.1246/cl.1991.761.

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22

Dyker, Gerald, Peter Grundt, Hardy Markwitz, and Gerald Henkel. "Heck Reaction and Robinson-Type Annulation: A Versatile Combination." Journal of Organic Chemistry 63, no. 17 (August 1998): 6043–47. http://dx.doi.org/10.1021/jo9803535.

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23

Koike, Tooru, Xiaoli Du, Tomoyuki Sanada, Yasuaki Danda, and Atsunori Mori. "Iridium-Catalyzed Mizoroki–Heck-Type Reaction of Organosilicon Reagents." Angewandte Chemie International Edition 42, no. 1 (January 3, 2003): 89–92. http://dx.doi.org/10.1002/anie.200390061.

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24

Shirakawa, Eiji, Xuejing Zhang, and Tamio Hayashi. "Mizoroki-Heck-Type Reaction Mediated by Potassium tert-Butoxide." Angewandte Chemie International Edition 50, no. 20 (April 6, 2011): 4671–74. http://dx.doi.org/10.1002/anie.201008220.

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25

Kurahashi, Takuya, Hiroshi Shinokubo, and Atsuhiro Osuka. "Intermolecular Rhodium-Catalyzed Carbometalation/Heck-Type Reaction in Water." Angewandte Chemie 118, no. 38 (September 25, 2006): 6484–86. http://dx.doi.org/10.1002/ange.200602585.

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26

Helaja, Juho, and Richard Goettlich. "ChemInform Abstract: A New Catalytic hetero-Heck Type Reaction." ChemInform 33, no. 33 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200233157.

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27

Shirakawa, Eiji, Xuejing Zhang, and Tamio Hayashi. "Mizoroki-Heck-Type Reaction Mediated by Potassium tert-Butoxide." Angewandte Chemie 123, no. 20 (April 6, 2011): 4767–70. http://dx.doi.org/10.1002/ange.201008220.

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28

Kurahashi, Takuya, Hiroshi Shinokubo, and Atsuhiro Osuka. "Intermolecular Rhodium-Catalyzed Carbometalation/Heck-Type Reaction in Water." Angewandte Chemie International Edition 45, no. 38 (September 25, 2006): 6336–38. http://dx.doi.org/10.1002/anie.200602585.

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29

Zheng, Meifang, Pengquan Chen, Wanqing Wu, and Huanfeng Jiang. "Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones." Chemical Communications 52, no. 1 (2016): 84–87. http://dx.doi.org/10.1039/c5cc06958k.

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30

Gudeika, Dalius, Gjergji Sini, Vygintas Jankauskas, Galyna Sych, and Juozas V. Grazulevicius. "Synthesis and properties of the derivatives of triphenylamine and 1,8-naphthalimide with the olefinic linkages between chromophores." RSC Advances 6, no. 3 (2016): 2191–201. http://dx.doi.org/10.1039/c5ra24820e.

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31

Zhang, Ji-Quan, Jun Cao, Wei Li, Shu-Min Li, Yong-Kang Li, Jian-Ta Wang, and Lei Tang. "Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines." New Journal of Chemistry 41, no. 2 (2017): 437–41. http://dx.doi.org/10.1039/c6nj03718f.

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32

Khodja, Walid, Alexandre Leclair, Jordi Rull-Barrull, Françoise Zammattio, Ksenia V. Kutonova, Marina E. Trusova, François-Xavier Felpin, and Mireia Rodriguez-Zubiri. "The promoting effect of pyridine ligands in the Pd-catalysed Heck–Matsuda reaction." New Journal of Chemistry 40, no. 10 (2016): 8855–62. http://dx.doi.org/10.1039/c6nj01717g.

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33

Yuan, Kedong, Rui Sang, Jean-François Soulé, and Henri Doucet. "Desulfitative Pd-catalysed coupling reaction using benzenesulfonyl chlorides and enones as the coupling partners." Catalysis Science & Technology 5, no. 5 (2015): 2904–12. http://dx.doi.org/10.1039/c5cy00089k.

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34

Miyake, Junpei, Masahiro Watanabe, and Kenji Miyatake. "Intrapolymer Heck reaction for proton conductive ladder-type aromatic block copolymers." RSC Adv. 4, no. 40 (2014): 21049–53. http://dx.doi.org/10.1039/c4ra02582b.

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A novel polymer synthetic method, intrapolymer Heck reaction, provided ladder-type ionomer membranes with excellent proton conductivity (221 mS cm⁻¹at 80 °C and 90% relative humidity) and mechanical strength over a wide range of humidity (ca.0–90% relative humidity) at 80 °C.

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35

Gao, Pei-Sen, Kan Zhang, Ming-Ming Yang, Shan Xu, Hua-Ming Sun, Jin-Lei Zhang, Zi-Wei Gao, Wei-Qiang Zhang, and Li-Wen Xu. "A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water." Chemical Communications 54, no. 40 (2018): 5074–77. http://dx.doi.org/10.1039/c8cc00324f.

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A novel and robust PEG-modulated s-triazine-based multifunctional and hydrophilic Schiff base/N,P-ligand L9 was employed in the Pd-catalyzed Heck-type carbonylative coupling reactions, yielding chalcone derivatives in good yields.

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36

Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, Haining Wang, Ning Chen, Wei Wei, Huiying Zeng, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (June 13, 2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenation, we envisioned and subsequently developed two unprecedented new types of chemical transformations: a) alcohol deoxygenation and b) C–C bond formations with various electrophiles including Grignard-type reaction, conjugate addition, olefination, and diverse cross-coupling reactions.1 Introduction2 Background3 Alcohol Deoxygenation3.1 Ir-Catalyzed Alcohol Deoxygenation3.2 Ru-Catalyzed Alcohol Deoxygenation3.3 Mn-Catalyzed Alcohol Deoxygenation4 Grignard-Type Reactions4.1 Ru-Catalyzed Addition of Hydrazones with Aldehydes and Ketones4.2 Ru-Catalyzed Addition of Hydrazone with Imines4.3 Ru-Catalyzed Addition of Hydrazone with CO2 4.4 Fe-Catalyzed Addition of Hydrazones5 Conjugate Addition Reactions5.1 Ru-Catalyzed Conjugate Addition Reactions5.2 Fe-Catalyzed Conjugate Addition Reactions6 Cross-Coupling Reactions6.1 Ni-Catalyzed Negishi-type Coupling6.2 Pd-Catalyzed Tsuji–Trost Alkylation Reaction7 Other Reactions7.1 Olefination7.2 Heck-Type Reaction7.3 Ullmann-Type Reaction8 Conclusion and Outlook

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37

Ikeda, Yousuke, Tomoaki Nakamura, Hideki Yorimitsu, and Koichiro Oshima. "Cobalt-Catalyzed Heck-Type Reaction of Alkyl Halides with Styrenes." Journal of the American Chemical Society 124, no. 23 (June 2002): 6514–15. http://dx.doi.org/10.1021/ja026296l.

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38

Matsude, Akihiro, Koji Hirano, and Masahiro Miura. "Palladium‐Catalyzed Intramolecular Mizoroki‐Heck‐Type Reaction of Diarylmethyl Carbonates." Advanced Synthesis & Catalysis 362, no. 3 (December 10, 2019): 518–22. http://dx.doi.org/10.1002/adsc.201901398.

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39

Ikeda, Yousuke, Hideki Yorimitsu, Hiroshi Shinokubo, and Koichiro Oshima. "Cobalt-Mediated Mizoroki-Heck-Type Reaction of Epoxide with Styrene." Advanced Synthesis & Catalysis 346, no. 13-15 (December 2004): 1631–34. http://dx.doi.org/10.1002/adsc.200404074.

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40

KURIHARA, Y., M. SODEOKA, and M. SHIBASAKI. "ChemInform Abstract: Asymmetric Heck-Type Reaction Utilizing Hypervalent Alkenyliodonium Salt." ChemInform 26, no. 24 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199524108.

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41

Yorimitsu, Hideki, and Koichiro Oshima. "New synthetic reactions catalyzed by cobalt complexes." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 441–49. http://dx.doi.org/10.1351/pac200678020441.

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Without suffering from β-elimination, cobalt complexes allow cross-coupling reactions of alkyl halides with Grignard reagents. A combination of a cobalt complex and trimethylsilylmethyl Grignard reagent effects Mizoroki-Heck-type reaction of alkyl halide with styrene, which conventional palladium catalysts have never made possible. Cobalt exhibits intriguing catalytic activities on hydrophosphination and allylzincation of alkynes. Silylmethylcobalt reagent is a powerful tool for the synthesis of highly silylated ethenes.

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42

Zhang, Yong, Ya-Kui Sun, Ya-Ping Chang, Hui Shao, and Yu-Ming Zhao. "Palladium-catalyzed cascade carbonylative annulation between alkene-tethered aryl iodides and carbon monoxide." Chemical Communications 57, no. 57 (2021): 7023–26. http://dx.doi.org/10.1039/d1cc02217b.

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A novel Pd-catalyzed carbonylative cascade of alkene-tethered aryl iodides has been developed. Mechanistic studies suggested the reaction proceeded via a Heck-type carbonylative cyclization, followed by a ketene-involved Friedel–Crafts acylation.

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43

Dziemidkiewicz, Anna, Martyna Pingot, and Magdalena Maciejewska. "METAL COMPLEXES AS NEW PRO-ECOLOGICAL CROSSLINKING AGENTS FOR CHLOROPRENE RUBBER BASED ON HECK COUPLING REACTION." Rubber Chemistry and Technology 92, no. 3 (July 1, 2019): 589–97. http://dx.doi.org/10.5254/rct.19.81465.

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ABSTRACT The influence of new pro-ecological curing agents on the crosslinking process of chloroprene rubber (CR) was examined. The proposed curing system used a simpler recipe (no need to apply harmful products such as zinc oxide and ethylene thiourea) and cost less than standard metal oxides. It was expected that the mechanism of crosslinking would be similar to that of Heck-type reactions. Heck-type reactions are powerful tools for the creation of new C=C bonds. They provide the simplest and most efficient way to synthesize a variety of important compounds used in many areas, such as pharmaceuticals, antioxidants, ultraviolet absorbers, and industrial applications. However, despite their wide application, Heck-type reactions have not been used in the rubber industry so far. Rubber blends containing acetylacetonates with different transition metals as new crosslinking agents were filled with fumed silica Aerosil 380 or carbon black Corax N-550. It was found that metal complexes are active crosslinking agents of the CR composites. The obtained vulcanizates were characterized by a high degree of crosslinking and good mechanical properties. Considering the high tensile strength and degree of crosslinking, iron acetylacetonate was the most effective curing agent of the used metal complexes. Compared with the reference sample cured with metal oxides, the CR samples crosslinked using metal acetylacetonates had a higher activity.

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44

Naik, Nilesh H., Tukaram D. Urmode, Arun K. Sikder, and Radhika S. Kusurkar. "Total Synthesis of Bouchardatine." Australian Journal of Chemistry 66, no. 9 (2013): 1112. http://dx.doi.org/10.1071/ch13331.

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Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-carbaldehyde (bouchardatine).

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45

Tarnowicz-Ligus, Stanisława, and Anna Trzeciak. "Heck Transformations of Biological Compounds Catalyzed by Phosphine-Free Palladium." Molecules 23, no. 9 (September 1, 2018): 2227. http://dx.doi.org/10.3390/molecules23092227.

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The development and optimization of synthetic methods leading to functionalized biologically active compounds is described. Two alternative pathways based on Heck-type reactions, employing iodobenzene or phenylboronic acid, were elaborated for the arylation of eugenol and estragole. Cinnamyl alcohol was efficiently transformed to saturated arylated aldehydes in reaction with iodobenzene using the tandem arylation/isomerization sequential process. The arylation of cinnamyl alcohol with phenylboronic acid mainly gave unsaturated alcohol, while the yield of saturated aldehyde was much lower. Catalytic reactions were carried out using simple, phosphine-free palladium precursors and water as a cosolvent, following green chemistry rules as much as possible.

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46

Glorius, Frank. "Palladium-catalyzed Heck-type reaction of 2-chloro acetamides with olefins." Tetrahedron Letters 44, no. 30 (July 2003): 5751–54. http://dx.doi.org/10.1016/s0040-4039(03)01377-7.

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47

Ohff, Manuela, Andreas Ohff, Milko E. van der Boom, and David Milstein. "Highly Active Pd(II) PCP-Type Catalysts for the Heck Reaction." Journal of the American Chemical Society 119, no. 48 (December 1997): 11687–88. http://dx.doi.org/10.1021/ja9729692.

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48

Zong, Zhenzhen, Wenxiao Wang, Xiaohui Bai, Hui Xi, and Zhiping Li. "Manganese-Catalyzed Alkyl-Heck-Type Reaction via Oxidative Decarbonylation of Aldehydes." Asian Journal of Organic Chemistry 4, no. 7 (May 14, 2015): 622–25. http://dx.doi.org/10.1002/ajoc.201500148.

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49

Shirakawa, Eiji, Xuejing Zhang, and Tamio Hayashi. "ChemInform Abstract: Mizoroki-Heck-Type Reaction Mediated by Potassium tert-Butoxide." ChemInform 42, no. 38 (August 25, 2011): no. http://dx.doi.org/10.1002/chin.201138100.

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50

Bettadapur, Kiran R., Mahadev Sharanappa Sherikar, Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "RhIII -Catalyzed C−H Activation: Mizoroki-Heck-Type Reaction of Maleimides." Asian Journal of Organic Chemistry 7, no. 7 (May 30, 2018): 1338–42. http://dx.doi.org/10.1002/ajoc.201800193.

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