Issue 10, 2019

A self-hydrosilylation of phosphanylhydrosilylalkynes promoted by B(C6F5)3? An experimental and mechanistic study

Abstract

Phosphanylhydrosilylalkynes Me2HSiC[triple bond, length as m-dash]CPAr2 (Ar = Ph, 1a; 4-MeC6H4, 1b) were synthesized, which reacted with B(C6F5)3 to produce alkenes [(E)-(C6F5)3BCH[double bond, length as m-dash]C(PAr2)SiMe2]2 (2a and 2b) and (Z)-(C6F5)2BCH[double bond, length as m-dash]C(PAr2)SiMe2(C6F5) (3a and 3b). The formation of 2a (or 2b) involved a Wrackmeyer's SiHMe2 migration followed by Si–H addition across the C[triple bond, length as m-dash]C bond, whereas, that of 3a (or 3b) involved a similar mechanism with a further C6F5 migration. The B(C6F5)3-promoted reaction of the Si-centered geminal H and C[triple bond, length as m-dash]C groups is thus realized, which may be considered as a self-hydrosilylation. Mechanistic studies by both variable temperature NMR spectroscopy and DFT calculations were accomplished.

Graphical abstract: A self-hydrosilylation of phosphanylhydrosilylalkynes promoted by B(C6F5)3? An experimental and mechanistic study

Supplementary files

Article information

Article type
Communication
Submitted
13 nov. 2018
Accepted
07 janv. 2019
First published
07 janv. 2019

Chem. Commun., 2019,55, 1494-1497

A self-hydrosilylation of phosphanylhydrosilylalkynes promoted by B(C6F5)3? An experimental and mechanistic study

Y. Huang, X. Wang, Y. Li, M. Yang, M. Su and H. Zhu, Chem. Commun., 2019, 55, 1494 DOI: 10.1039/C8CC09022J

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