Abstract
The alkenylzincation of internal alkynes is an effective method for the
synthesis of multi-substituted conjugated dienes; however, the current
catalytic systems for this reaction are limited in terms of substrate
scope and selectivity control, which restricts its practical
applications. Herein, we report the first iron-catalyzed
alkenylzincation of internal alkynes, which features mild conditions,
simple oper-ation, broad substrate scope (including aryl/alkyl, diaryl,
and dialkyl acetylenes), excellent functional group tolerance
(tolerating highly active functional groups such as ester, methylthio,
amide, sulfonyl, cyano, etc), and high activity (with a turnover number
of up to 11500, the highest record for carbometallation reactions).
Notably, the catalytic system described in this article also realized
the highly selective vinylzincation of unfunctionalized internal alkynes
as well as the alkenylzincation of unsymmetrical diarylacetylenes and
dial-kyl acetylenes, which have not been achieved with other catalytic
systems reported in the literatures. The current study provides a highly
selective access to synthetically important multi-substituted conjugated
dienes.