Organic Letters
Organic Letters
5 years ago

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

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
Yan-dong Wu, An-xin Wu, Xiao Geng, Xia Wu, Peng Zhao, Jingjing Zhang, Xingxing Gong
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01492

DOI: 10.1021/acs.orglett.7b01492

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