Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source

Journal of the American Chemical Society
Xingjie ZhangYuanhong Liu

Abstract

The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.

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Citations

Sep 26, 2019·Chemistry : a European Journal·David TejedorFernando García-Tellado
Apr 3, 2020·Chemistry : a European Journal·Feilong SunXianjie Fang
May 21, 2020·Chemical Communications : Chem Comm·Feilong SunXianjie Fang
Dec 18, 2019·Organic & Biomolecular Chemistry·Hongru ZhangKaiwu Dong
Apr 30, 2019·Organic & Biomolecular Chemistry·Hiroto HoriAtsushi Nishida
Jan 19, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Dandan JiangLili Zhao
May 21, 2020·Angewandte Chemie·Dingyuan YanBen Zhong Tang
Apr 10, 2021·Journal of the American Chemical Society·Xiang LyuSukbok Chang
May 11, 2021·The Journal of Organic Chemistry·Yuze DaiBaomin Fan
Oct 10, 2019·The Journal of Organic Chemistry·Roman S MalykhinAlexey Yu Sukhorukov
May 12, 2020·Organic Letters·Nils L FryeArmido Studer
Oct 23, 2018·The Journal of Organic Chemistry·Yi GanYuanhong Liu
Jan 5, 2021·The Journal of Organic Chemistry·Alexander BärRainer Schobert
Jun 2, 2020·Journal of the American Chemical Society·Benjamin N BhawalBill Morandi
Jan 16, 2020·Journal of the American Chemical Society·Naoki MiwaTakashi Nishikata
Jan 9, 2020·Organic Letters·Jinguo LongXianjie Fang
May 11, 2019·Organic Letters·Wang WangGuoyin Yin

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