Cobalt-Catalyzed Regioselective Olefin Isomerization Under Kinetic Control

Journal of the American Chemical Society
Xufang LiuQiang Liu

Abstract

Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin isomerization reaction. By taking the advantage of fine-tunable NNP-pincer ligand structures, this catalytic system features high kinetic control of regioselectivity. This mild catalytic system enables the isomerization of 1,1-disubstituted olefins bearing a wide range of functional groups in excellent yields and regioselectivity. The synthetic utility of this transformation was highlighted by the highly selective preparation of a key intermediate for the total synthesis of minfiensine. Moreover, a new strategy was developed to realize the selective monoisomerization of 1-alkenes to 2-alkenes dictated by installing substituents on the γ-position of the double bonds. Mechanistic studies supported that the in situ generated Co-H species underwent migratory insertion of double bond/β-H elimination sequence to afford the isomerizati...Continue Reading

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Citations

Nov 1, 2018·Chemistry : a European Journal·Thomas M MaierRobert Wolf
Jan 24, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Matthew V GradiskiRobert H Morris
Apr 12, 2019·Chemistry : a European Journal·Brian SpiegelbergJohannes G de Vries
Jun 25, 2019·Angewandte Chemie·John J MolloyRyan Gilmour
Jan 22, 2020·Chemical Communications : Chem Comm·Weiwei GaoShengtao Ding
Mar 3, 2020·Angewandte Chemie·Xufang LiuQiang Liu
Feb 7, 2020·Chemistry : a European Journal·Enrico BergamaschiChristopher J Teskey
Sep 26, 2020·Organic & Biomolecular Chemistry·Chiara FaverioMaurizio Benaglia
Dec 13, 2019·Chemical Communications : Chem Comm·Timothy M BoydAndrew S Weller
Jan 27, 2019·Science·Ajoy KapatFranziska Schoenebeck
Mar 6, 2019·Angewandte Chemie·Qing-Yuan MengBurkhard König
Jan 23, 2021·Chemical Society Reviews·Jialin WenXumu Zhang
Feb 9, 2021·Journal of the American Chemical Society·Andrew M CampAlexander J M Miller
Feb 18, 2021·Journal of the American Chemical Society·Daniel KimPatrick L Holland
Jul 23, 2020·Organic Letters·Shicheng ShiJack R Norton
Feb 12, 2020·Organic Letters·Wenlong RenYian Shi
Apr 22, 2020·Journal of the American Chemical Society·Sheng ZhangMichael Findlater
Oct 1, 2020·Journal of the American Chemical Society·Xiaolong YuMing Joo Koh
Oct 26, 2018·Journal of the American Chemical Society·Rui-Zhi HuangYu Zhao
Jan 10, 2020·Organic Letters·Jiajin ZhaoZhan Lu
Sep 29, 2021·Organic Letters·Yaqin LeiWanxiang Zhao
Dec 7, 2021·Journal of the American Chemical Society·Xufang LiuQiang Liu

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