Rhodium-Catalyzed Reductive Carbonylative Cyclization of Aryl Alkynes with Hydrosilanes via C–H Activation to Access Silyl-Substituted Indanones

TL;DR

This paper presents a new rhodium-catalyzed method to efficiently create silyl-substituted indanones from aryl alkynes and hydrosilanes using carbon monoxide.

Contribution

A novel catalytic method for synthesizing silyl-substituted indanones via C–H activation and carbonylation is introduced.

Findings

The method achieves high regioselectivity and works with a wide range of symmetrical and unsymmetrical alkynes.

Mechanistic studies suggest a pathway involving hydrosilylation, C–H activation, and carbonylation.

The reaction provides a practical route to valuable organosilicon compounds.

Abstract

A rhodium-catalyzed reductive carbonylative cyclization
for the
direct synthesis of 3-silyl-1-indanones from readily available aryl
alkynes and hydrosilanes is described. This transformation concurrently
introduces a silicon moiety and constructs the indanone core under
an atmosphere of carbon monoxide, exhibiting high regioselectivity.
The reaction features a broad substrate scope across a range of symmetrical
and unsymmetrical alkynes as well as diverse hydrosilanes. Preliminary
mechanistic studies support a pathway involving hydrosilylation, rate-limiting
C–H activation, and carbonylation. This work provides a concise
and practical route to valuable organosilicon scaffolds.

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