Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**

Gao, Yang; Yazdani, Sima; Kendrick, IV, Aaron; Junor, Glen P.; Kang, Taeho; Grotjahn, Douglas B.; Bertrand, Guy; Jazzar, Rodolphe; Engle, Keary M.

doi:10.1002/ange.202106107

Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**

Journal Article · Thu Jul 29 00:00:00 EDT 2021 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.202106107· OSTI ID:1909306

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Department of Chemistry The Scripps Research Institute 10550 N Torrey Pines Road La Jolla CA 92037-1000 USA
Department of Chemistry and Biochemistry University of California, San Diego UCSD-CNRS Joint Research Laboratory (IRL 3555) La Jolla CA 92093-0358 USA, Department of Chemistry and Biochemistry San Diego State University 5500 Campanile Drive San Diego CA 92182-1030 USA
Department of Chemistry and Biochemistry University of California, San Diego UCSD-CNRS Joint Research Laboratory (IRL 3555) La Jolla CA 92093-0358 USA
Department of Chemistry and Biochemistry San Diego State University 5500 Campanile Drive San Diego CA 92182-1030 USA

Abstract

Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or reagents, with general solutions lacking. Herein, we describe a selective copper‐catalyzed Markovnikov hydrofunctionalization of terminal alkynes that is facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. Using this method, both alkyl‐ and aryl‐substituted alkynes are coupled with a variety of boryl and silyl reagents with high α‐selectivity. The reaction is scalable, and the products are versatile intermediates that can participate in various downstream transformations. Preliminary mechanistic experiments shed light on the role of CAAC ligands in this process.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0009376

OSTI ID:: 1909306

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 36 Vol. 133; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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