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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Published on: October 18, 2019

Rhodium-Catalyzed Intermolecular Silylation of C_sp -H by Silacyclobutanes

Tao He¹, Bin Li¹, Lichuan Liu¹

¹School of Pharmaceutical Sciences, MOE Key Laboratory of, Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, 100084, Beijing, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|February 1, 2021

Abstract:

The signature reactivity of silacyclobutane (SCB) is their cycloaddition reactions with various π bonds. Recently, the first cases were disclosed where SCBs reacted with both C_sp2 -H and C_sp3 -H σ bonds in an intramolecular fashion. Herein, it is reported that SCB is also an efficient reagent for C_sp -H bond silylation. Thus, rhodium-catalyzed intermolecular reactions between SCBs and terminal alkynes produced a series of symmetrical and unsymmetrical tetraorganosilicons bearing a C_sp -Si functionality. Preliminary studies suggested that the reaction did not involve a cycloaddition pathway, but instead a direct activation of C_sp -H bonds.

Keywords:

C−Si bond activation alkynes rhodium silane synthetic methods

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