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CO as a C1 Source: B(CF)-Catalyzed Cyclization of o-Phenylene-diamines To Construct Benzimidazoles in the Presence of Hydrosilane. | LitMetric

CO as a C1 Source: B(CF)-Catalyzed Cyclization of o-Phenylene-diamines To Construct Benzimidazoles in the Presence of Hydrosilane.

Org Lett

State Key Laboratory for Oxo Synthesis and Selective Oxidation, and Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences , Lanzhou 730000, P. R. China.

Published: December 2016

The catalytic construction of benzimidazoles using CO as a carbon source represents a facile and sustainable approach to obtaining these valuable compounds. Herein, we describe the B(CF)-catalyzed synthesis of benzimidazoles via cyclization of o-phenylenediamines with CO and PhSiH. This metal-free catalytic route achieves the desired products in high yield under convenient reaction conditions and is applicable to a broad substrate scope. A plausible mechanism for the reaction involving a frustrated Lewis pair pathway is proposed based on spectroscopic characterization (e.g., C NMR) of the reaction intermediates.

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Source
http://dx.doi.org/10.1021/acs.orglett.6b03030DOI Listing

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