Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**
Abstract
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.
- Authors:
-
[1];
[2];
[1];
[3];
[1];
[4];
[3];
[3];
[1]
- 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
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1909306
- Grant/Contract Number:
- SC0009376
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Angewandte Chemie
- Additional Journal Information:
- Journal Name: Angewandte Chemie Journal Volume: 133 Journal Issue: 36; Journal ID: ISSN 0044-8249
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Gao, Yang, Yazdani, Sima, Kendrick, IV, Aaron, Junor, Glen P., Kang, Taeho, Grotjahn, Douglas B., Bertrand, Guy, Jazzar, Rodolphe, and Engle, Keary M. Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**. Germany: N. p., 2021.
Web. doi:10.1002/ange.202106107.
Gao, Yang, Yazdani, Sima, Kendrick, IV, Aaron, Junor, Glen P., Kang, Taeho, Grotjahn, Douglas B., Bertrand, Guy, Jazzar, Rodolphe, & Engle, Keary M. Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**. Germany. https://doi.org/10.1002/ange.202106107
Gao, Yang, Yazdani, Sima, Kendrick, IV, Aaron, Junor, Glen P., Kang, Taeho, Grotjahn, Douglas B., Bertrand, Guy, Jazzar, Rodolphe, and Engle, Keary M. Thu .
"Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**". Germany. https://doi.org/10.1002/ange.202106107.
@article{osti_1909306,
title = {Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**},
author = {Gao, Yang and Yazdani, Sima and Kendrick, IV, Aaron and Junor, Glen P. and Kang, Taeho and Grotjahn, Douglas B. and Bertrand, Guy and Jazzar, Rodolphe and Engle, Keary M.},
abstractNote = {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.},
doi = {10.1002/ange.202106107},
journal = {Angewandte Chemie},
number = 36,
volume = 133,
place = {Germany},
year = {Thu Jul 29 00:00:00 EDT 2021},
month = {Thu Jul 29 00:00:00 EDT 2021}
}
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