Electrochemical Alkynyl/Alkenyl Migration for the Radical Difunctionalization of Alkenes.

Gao, Yongyuan; Mei, Haibo; Han, Jianlin; Pan, Yi

An efficient electrochemical 1,2‐sulfonylation/alkynylation of alkenes via radical 1,4‐alkynyl migration of alkynyl‐substituted tertiary alcohols is described, which used sodium sulfinates as sulfonyl sources affording the corresponding α‐sulfonyl‐β‐alkynylated products in moderate to excellent yields. This electrochemical reaction proceeds smoothly without the use of any metal catalyst, additive and oxidant and thus represents a new and eco‐friendly strategy for the difunctionalization of unactive olefins, and also the first example of the electrochemical distal radical migration reaction. No additives required: An efficient electrochemical 1,2‐sulfonylation/alkynylation of alkenes via radical 1,4‐alkynyl migration of alkynyl‐substituted tertiary alcohols is described that uses sodium sulfinates as sulfonyl sources and requires no metal catalyst, additive, or oxidant, and gives the corresponding α‐sulfonyl‐β‐alkynylated products in moderate to excellent yields.

ELECTROCHEMISTRY; EMIGRATION & immigration; ALKENES; ALCOHOLS (Chemical class); OXIDIZING agents; METAL catalysts

Chemistry - A European Journal, 2018, Vol 24, Issue 65, p17205

0947-6539

Academic Journal

10.1002/chem.201804157