- Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N-Tosyl Vinylaziridines with Difluoroalkyl Halides
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A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6πelectrocyclization, and defluorinated aromatization.
- Liu, Yantao,Luo, Wen,Wang, Zhenjie,Zhao, Yuxin,Zhao, Jingjing,Xu, Xuejun,Wang, Chaojie,Li, Pan
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supporting information
p. 9658 - 9664
(2020/12/21)
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- Modular pyridine synthesis from oximes and enals through synergistic copper/iminium catalysis
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We describe here a [3+3]-type condensation reaction of O-acetyl ketoximes and α,β-unsaturated aldehydes that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine). This redox-neutral reaction allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst, which would initially reduce the oxime N-O bond to generate a nucleophilic copper(II) enamide and later oxidize a dihydropyridine intermediate to the pyridine product.
- Wei, Ye,Yoshikai, Naohiko
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supporting information
p. 3756 - 3759
(2013/04/23)
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- 2-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone
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The present invention is directed to certain piperidine, pyrrolidine, and hexahydro-1H-azepine compounds of the general structural formula: STR1 wherein R1, R3, R4, R5, A, W, X, Y, and n axe as defined herein. T
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