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Direct Oxidative Cleavage of Multiple Csp3–H Bonds and a C–C Bond in 2-(Pyridin-2-yl)acetate Derivatives: Formal [3 + 1 + 1] Synthesis of 3-(Pyridin-2-yl)indolizine Skeletons

Author:
Wu, Xia, Zhao, Peng, Geng, Xiao, Zhang, Jingjing, Gong, Xingxing, Wu, Yan-dong, Wu, An-xin
Source:
Organic letters 2017 v.19 no.12 pp. 3319-3322
ISSN:
1523-7052
Subject:
chemical bonding, chemical reactions, chemical structure, indolizines, ketones, pyridines
Abstract:
A novel iodine-promoted oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and methyl ketones via the cleavage of multiple Cₛₚ₃–H bonds has been developed, which also achieved efficient cleavage of a C–C bond in the 2-(pyridin-2-yl)acetate derivatives. This protocol represents an elegant molecular fragment assembly of diverse 3-(pyridin-2-yl)indolizines via a formal [3 + 1 + 1] annulation. Notably, the pyridine derivatives serve two pivotal roles to provide two fragments to construct 3-(pyridin-2-yl)indolizine skeletons, rather than the single role in building common indolizines.
Agid:
5793044