NH-Directed C-H Alkenylation of 2-Vinylanilines with Vinylbenziodoxolones.

Org Lett

Institute for Organic and Analytical Chemistry, University of Bremen, 28359 Bremen, Germany.

Published: October 2017

The first directing-group-mediated C-H alkenylation with alkenyl-λ-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an Ir catalyst enabled the synthesis of highly desirable 1,3-dienes in excellent yields of up to 98% with high to perfect (Z,E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.

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http://dx.doi.org/10.1021/acs.orglett.7b02630DOI Listing

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