Rhodium(I)‐Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion

Publisher: John Wiley & Sons Inc

E-ISSN: 1521-3773|54|27|7891-7894

ISSN: 1433-7851

Source: ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.54, Iss.27, 2015-06, pp. : 7891-7894

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Abstract

AbstractA RhI‐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(sp3) and C(sp3)C(sp3) bonds are built successively on the carbenic carbon atom. The RhI‐carbene migratory insertion of an alkynyl moiety and subsequent alkylation are proposed to account for the two separate CC bond formations. This reaction provides an efficient and tunable method for the construction of all‐carbon quaternary center.