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Radical Carbonyl Propargylation by Dual Catalysis
Author(s) -
Huang HuanMing,
Bellotti Peter,
Daniliuc Constantin G.,
Glorius Frank
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011996
Subject(s) - moiety , chemistry , catalysis , combinatorial chemistry , ionic bonding , organic chemistry , photochemistry , ion
Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3‐enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all‐carbon quaternary centers could be obtained by a catalytic radical three‐component coupling of 1,3‐enynes, aldehydes and suitable radical precursors (41 examples). This redox‐neutral multi‐component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench‐stable, non‐toxic, and inexpensive CrCl 3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical‐polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.