Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations

Shigeru Arai; Koichi Nakazawa; Xiao-Fei Yang; Masaya Nakajima; Shinji Harada; Atsushi Nishida

doi:10.1039/D4OB00380B

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Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations†

Shigeru Arai,

*^ab Koichi Nakazawa,^a Xiao-Fei Yang,^a Masaya Nakajima,^ac Shinji Harada

^abd and Atsushi Nishida^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, Japan
E-mail: araisgr@chiba-u.jp
Tel: +81-43-226-2913

^b Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba, Japan

^c Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

^d Institute for Advanced Academic Research, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

We have developed a nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates that gives syn-β-cyanoalkenes. DFT calculations suggest that a favored transition state promotes Cα–H bond formation for determining regio- and stereoselectivity of the products.

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Article information

DOI: https://doi.org/10.1039/D4OB00380B
Article type: Communication
Submitted: 08 Mar 2024
Accepted: 09 Apr 2024
First published: 16 Apr 2024

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Org. Biomol. Chem., 2024, Advance Article

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Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations

S. Arai, K. Nakazawa, X. Yang, M. Nakajima, S. Harada and A. Nishida, Org. Biomol. Chem., 2024, Advance Article , DOI: 10.1039/D4OB00380B

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Organic & Biomolecular Chemistry

Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations†

Abstract

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Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations

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