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Rhodium(I)‐Catalyzed Sequential C(sp)C(sp 3 ) and C(sp 3 )C(sp 3 ) Bond Formation through Migratory Carbene Insertion
Author(s) -
Xia Ying,
Feng Sheng,
Liu Zhen,
Zhang Yan,
Wang Jianbo
Publication year - 2015
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.201503140
Subject(s) - carbene , migratory insertion , alkyl , chemistry , medicinal chemistry , halide , catalysis , alkylation , moiety , insertion reaction , rhodium , coupling reaction , stereochemistry , organic chemistry
A Rh I ‐catalyzed three‐component reaction of tert ‐propargyl alcohol, diazoester, and alkyl halide has been developed. This reaction can be considered as a carbene‐involving sequential alkyl and alkynyl coupling, in which C(sp)C(sp 3 ) and C(sp 3 )C(sp 3 ) bonds are built successively on the carbenic carbon atom. The Rh I ‐carbene migratory insertion of an alkynyl moiety and subsequent alkylation are proposed to account for the two separate CC bond formations. This reaction provides an efficient and tunable method for the construction of all‐carbon quaternary center.