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Journal articles on the topic 'N-Aryl aldimines'

Author: Grafiati

Published: 25 May 2024

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1

Beng, Timothy K., Jorge Garcia, Jane Eichwald, and Claire Borg. "Introducing a sulfone-embedded anhydride to the anhydride-imine reaction for the modular synthesis of N-heterocyclic sulfones bearing vicinal stereocenters." RSC Advances 13, no. 21 (2023): 14355–60. http://dx.doi.org/10.1039/d3ra01812a.

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2

Denmark, Scott, and Hyung Chi. "Synthesis of 2-Alkenyl-Tethered Anilines." Synthesis 49, no. 13 (May 4, 2017): 2873–88. http://dx.doi.org/10.1055/s-0036-1589002.

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Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

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3

Li, Yang, Bi-Jie Li, Wen-Hua Wang, Wei-Ping Huang, Xi-Sha Zhang, Kang Chen, and Zhang-Jie Shi. "Rhodium-Catalyzed Direct Addition of Aryl CH Bonds to N-Sulfonyl Aldimines." Angewandte Chemie International Edition 50, no. 9 (January 26, 2011): 2115–19. http://dx.doi.org/10.1002/anie.201007464.

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4

Li, Yang, Bi-Jie Li, Wen-Hua Wang, Wei-Ping Huang, Xi-Sha Zhang, Kang Chen, and Zhang-Jie Shi. "Rhodium-Catalyzed Direct Addition of Aryl CH Bonds to N-Sulfonyl Aldimines." Angewandte Chemie 123, no. 9 (January 26, 2011): 2163–67. http://dx.doi.org/10.1002/ange.201007464.

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5

Seth, Dipravath Kumar, and Samaresh Bhattacharya. "Copper(I) complexes of N-(aryl)pyridine-2-aldimines: Spectral, electrochemical and catalytic properties." Polyhedron 30, no. 15 (September 2011): 2438–43. http://dx.doi.org/10.1016/j.poly.2011.05.037.

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6

Li, Yang, Bi-Jie Li, Wen-Hua Wang, Wei-Ping Huang, Xi-Sha Zhang, Kang Chen, and Zhang-Jie Shi. "ChemInform Abstract: Rhodium-Catalyzed Direct Addition of Aryl C-H Bonds to N-Sulfonyl Aldimines." ChemInform 42, no. 26 (June 3, 2011): no. http://dx.doi.org/10.1002/chin.201126087.

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7

Zhao, Gui-Ling, and Min Shi. "Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one." Organic & Biomolecular Chemistry 3, no. 20 (2005): 3686. http://dx.doi.org/10.1039/b510572b.

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8

Paul, Piyali, and Samaresh Bhattacharya. "Iridium mediated N–H and C–H bond activation of N-(aryl)pyrrole-2-aldimines. Synthesis, structure and, spectral and electrochemical properties." Journal of Organometallic Chemistry 713 (August 2012): 72–79. http://dx.doi.org/10.1016/j.jorganchem.2012.04.023.

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9

Mitra, Kamala, Subhendu Biswas, Shyamal Kumar Chattopadhyay, C. Robert Lucas, and Bibhutosh Adhikary. "Synthesis and X-ray Crystal Structures of Two Luminescent Imidazopyridinium Derivatives from the Corresponding N-(aryl)-Pyridine-2-aldimines." Journal of Chemical Crystallography 37, no. 8 (June 21, 2007): 567–71. http://dx.doi.org/10.1007/s10870-007-9212-y.

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10

Curti, Claudio, Lucia Battistini, Beatrice Ranieri, Giorgio Pelosi, Gloria Rassu, Giovanni Casiraghi, and Franca Zanardi. "ChemInform Abstract: anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines." ChemInform 42, no. 27 (June 9, 2011): no. http://dx.doi.org/10.1002/chin.201127115.

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11

Ishiyama, Tatsuo, and John Hartwig. "ChemInform Abstract: A Heck-Type Reaction Involving Carbon-Heteroatom Double Bonds. Rhodium(I)-Catalyzed Coupling of Aryl Halides with N-Pyrazyl Aldimines." ChemInform 32, no. 16 (April 17, 2001): no. http://dx.doi.org/10.1002/chin.200116114.

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12

Tomaszewski, MJ, J. Warkentin, and NH Werstiuk. "Free-Radical Chemistry of Imines." Australian Journal of Chemistry 48, no. 2 (1995): 291. http://dx.doi.org/10.1071/ch9950291.

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Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group. When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated. However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines. Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered. Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.

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13

Dey, Bikash Kali, Jayita Dutta, Michael G. B. Drew, and Samaresh Bhattacharya. "Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. Synthesis, characterization and catalytic application in C–C cross-coupling of arylaldehydes with arylboronic acids." Journal of Organometallic Chemistry 750 (January 2014): 176–84. http://dx.doi.org/10.1016/j.jorganchem.2013.11.019.

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14

Dey, Bikash Kali, Jayita Dutta, Michael G. B. Drew, and Samaresh Bhattacharya. "ChemInform Abstract: Chloro-Ruthenium Complexes with Carbonyl and N-(Aryl)pyridine-2-aldimines as Ancillary Ligands. Synthesis, Characterization and Catalytic Application in C-C Cross-Coupling of Arylaldehydes with Arylboronic Acids." ChemInform 45, no. 30 (July 10, 2014): no. http://dx.doi.org/10.1002/chin.201430081.

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15

Crousse, Benoît, Jean-Pierre Bégué, and Danièle Bonnet-Delpon. "Synthesis of 2-CF3-Tetrahydroquinoline and Quinoline Derivatives from CF3-N-Aryl-aldimine." Journal of Organic Chemistry 65, no. 16 (August 2000): 5009–13. http://dx.doi.org/10.1021/jo9918807.

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16

Goswami, Sreebrata, Wancydora Kharmawphlang, Alok K. Deb, and Shie-Ming Peng. "Monovalent copper complexes of N-aryl-pyridine-2-aldimine. synthesis, characterization and structure." Polyhedron 15, no. 20 (July 1996): 3635–41. http://dx.doi.org/10.1016/0277-5387(96)00065-4.

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17

Wang, Shang-Hua, and Rong-Jie Chein. "(Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine." Tetrahedron 72, no. 21 (May 2016): 2607–15. http://dx.doi.org/10.1016/j.tet.2014.12.063.

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18

Lucas, C. Robert, Kamala Mitra, Subhendu Biswas, Shyamal Kumar Chattopadhyay, and Bibhutosh Adhikary. "Synthesis, spectroscopy and redox properties of mononuclear manganese(II) and manganese(IV) complexes with N-(aryl)-pyridine-2-aldimine (L) and its amide derivatives. X-ray structural characterization of [Mn(MeL)2(NCS)2] (MeL = N-(4-methylphenyl)-pyridine-2-aldimine)." Transition Metal Chemistry 30, no. 2 (March 2005): 185–90. http://dx.doi.org/10.1007/s11243-004-3225-6.

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19

Nath Mitra, Kedar, Subrata Choudhury, Sreebrata Goswami, and Shie-Ming Peng. "A family of mixed ligand complexes of RuII-L [L = N-aryl-pyridine-2-aldimine], their reactions, isolation and characterization. X-ray crystal structure of [Ru(pic)(L1)2][ClO4]· CH2Cl2 [pic= 2-picolinate ion]." Polyhedron 16, no. 10 (March 1997): 1605–14. http://dx.doi.org/10.1016/s0277-5387(96)00482-2.

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20

Mishra, Dipankar, Subhendu Naskar, Bibhutosh Adhikary, Raymond J. Butcher, and Shyamal Kumar Chattopadhyay. "Synthesis, spectroscopic and electrochemical properties of some heteroleptic tris-chelates of ruthenium (II) involving 2,2′-bipyridine (bpy) and N-(aryl) pyridine-2-aldimine(L): X-ray crystal structures of [Ru(bpy)(L2)2](ClO4)2·H2O and 3-N(4-tolyl) imidazo [1,5a] pyridinium perchlorate." Polyhedron 24, no. 2 (January 2005): 201–8. http://dx.doi.org/10.1016/j.poly.2004.11.011.

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21

"Stereoselective Vinylation of Aryl N-(2-Pyridylsulfonyl) Aldimines." Synfacts 8, no. 03 (February 20, 2012): 0308. http://dx.doi.org/10.1055/s-0031-1290214.

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22

Chandra, Anushri, Papu Dhibar, Pragna Dutta, Piyali Paul, and Samaresh Bhattacharya. "N-(aryl)pyrrole-2-aldimine complexes of ruthenium: Synthesis, structure and, spectral and electrochemical properties." New Journal of Chemistry, 2023. http://dx.doi.org/10.1039/d2nj05295d.

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Abstract: Reaction of [Ru(dmso)4Cl2] with N-(4′-R-phenyl)pyrrole-2-aldimines (abbreviated as HL-R; where H depicts the dissociable pyrrole N-H proton and R = OCH3, CH3, H and Cl) in refluxing toluene in the...

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23

Deng, Yu-Qin, Qi-Qi Yan, Ting-Ting Zhang, Yi Zhou, Cheng-Yu He, and Quan-Zhong Liu. "Copper-Catalyzed Asymmetric Allylation of N-Aryl Aldimines." Journal of Organic Chemistry, December 11, 2023. http://dx.doi.org/10.1021/acs.joc.3c02035.

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24

Li, Zhenjiang, Xinhua Ren, Yuhu Shi, and Pingkai Ouyang. "Practical and General Entry to N-Tosyl Aryl Aldimines Promoted by Sulfamic Acid in Water and Alcohol." ChemInform 38, no. 31 (July 31, 2007). http://dx.doi.org/10.1002/chin.200731059.

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25

Esquivias, Jorge, Ramon Gomez Arrayas, and Juan Carlos Carretero. "ChemInform Abstract: Alkylation of Aryl N-(2-Pyridylsulfonyl)aldimines with Organozinc Halides: Conciliation of Reactivity and Chemoselectivity." ChemInform 39, no. 15 (April 8, 2008). http://dx.doi.org/10.1002/chin.200815070.

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26

Chen, Donghuang, Clément Lepori, Régis Guillot, Richard Gil, Sophie Bezzenine, and Jérôme Hannedouche. "A Rationally Designed Iron(II) Catalyst for C(sp3)−C(sp2) and C(sp3)−C(sp3) Suzuki−Miyaura Cross‐Coupling." Angewandte Chemie International Edition, May 22, 2024. http://dx.doi.org/10.1002/anie.202408419.

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Despite the paramount importance of the Suzuki‐Miyaura coupling (SMC) in academia and industry, and the great promise of iron to offer sustainable catalysis, iron‐catalyzed SMC involving sp3‐hybridized partners is still in its infancy. We herein report the development of a versatile, well‐defined electron‐deficient anilido‐aldimine iron(II) catalyst. This catalyst effectively performed C(sp3)‐C(sp2) and C(sp3)‐C(sp3) SMC of alkyl halide electrophiles and (hetero)aryl boronic ester and alkyl borane nucleophiles respectively, in the presence of a lithium amide base. These couplings operated under mild reaction conditions and displayed wide functional group compatibility including various medicinally relevant N‐, O‐ and S‐based heterocycles. They also tolerated primary, secondary and tertiary alkyl halides (Br, Cl, I), electron‐neutral, ‐rich and ‐poor boronic esters and primary and secondary alkyl boranes. Our methodology could be directly and efficiently applied to synthesize key intermediates relevant to pharmaceuticals and a potential drug candidate. For C(sp3)‐C(sp2) couplings, radical probe experiments militated in favor of a carbon‐centered radical derived from the electrophile. At the same time, reactions run with a pre‐formed activated boron nucleophile coupled to competition experiments supported the involvement of neutral, rather than an anionic, (hetero)aryl boronic ester in the key transmetalation step.

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27

Chen, Donghuang, Clément Lepori, Régis Guillot, Richard Gil, Sophie Bezzenine, and Jérôme Hannedouche. "A Rationally Designed Iron(II) Catalyst for C(sp3)−C(sp2) and C(sp3)−C(sp3) Suzuki−Miyaura Cross‐Coupling." Angewandte Chemie, May 22, 2024. http://dx.doi.org/10.1002/ange.202408419.

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Abstract:

Despite the paramount importance of the Suzuki‐Miyaura coupling (SMC) in academia and industry, and the great promise of iron to offer sustainable catalysis, iron‐catalyzed SMC involving sp3‐hybridized partners is still in its infancy. We herein report the development of a versatile, well‐defined electron‐deficient anilido‐aldimine iron(II) catalyst. This catalyst effectively performed C(sp3)‐C(sp2) and C(sp3)‐C(sp3) SMC of alkyl halide electrophiles and (hetero)aryl boronic ester and alkyl borane nucleophiles respectively, in the presence of a lithium amide base. These couplings operated under mild reaction conditions and displayed wide functional group compatibility including various medicinally relevant N‐, O‐ and S‐based heterocycles. They also tolerated primary, secondary and tertiary alkyl halides (Br, Cl, I), electron‐neutral, ‐rich and ‐poor boronic esters and primary and secondary alkyl boranes. Our methodology could be directly and efficiently applied to synthesize key intermediates relevant to pharmaceuticals and a potential drug candidate. For C(sp3)‐C(sp2) couplings, radical probe experiments militated in favor of a carbon‐centered radical derived from the electrophile. At the same time, reactions run with a pre‐formed activated boron nucleophile coupled to competition experiments supported the involvement of neutral, rather than an anionic, (hetero)aryl boronic ester in the key transmetalation step.

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28

Wang, Shang-Hua, and Rong-Jie Chein. "ChemInform Abstract: (Thiolan-2-yl)diphenylmethyl Benzyl Ether/N,N′-Diarylurea Cocatalyzed Asymmetric Aziridination of Cinnamyl Bromide and Aryl Aldimine." ChemInform 47, no. 38 (September 2016). http://dx.doi.org/10.1002/chin.201638022.

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