Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

Angewandte Chemie
Matteo ChierchiaJames P Morken

Abstract

A hybrid transition-metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds.

References

Jul 6, 2002·Organic Letters·Aiwen Lei, Xumu Zhang
Jun 28, 2008·Organic Letters·Yoshizumi YasuiYoshiji Takemoto
Oct 31, 2008·Organic & Biomolecular Chemistry·Katrina H Jensen, Matthew S Sigman
Mar 26, 2011·Organic Letters·Xiaolong YuHegui Gong
Jun 24, 2011·Angewandte Chemie·Eva Hevia, Robert E Mulvey
Nov 23, 2012·Journal of the American Chemical Society·Tao XuGuangbin Dong
Feb 13, 2014·Angewandte Chemie·Laetitia SouillartNicolai Cramer
Mar 1, 2014·Journal of the American Chemical Society·Huan Cong, Gregory C Fu
May 16, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aydin Demircan
Jun 26, 2014·Chemical Communications : Chem Comm·Guanghui ZhangAiwen Lei
May 20, 2015·Journal of the American Chemical Society·Béatrice Quiclet-Sire, Samir Z Zard
Nov 14, 2015·Journal of the American Chemical Society·Wei You, M Kevin Brown
Feb 18, 2016·Chemical Reviews·Liang HongRui Wang
Aug 5, 2016·Accounts of Chemical Research·Christopher R Jamison, Larry E Overman
Sep 9, 2016·Angewandte Chemie·Ji-Wei GuXingang Zhang
Dec 10, 2016·Journal of the American Chemical Society·Fei WangGuosheng Liu
Mar 4, 2017·Science·Marvin KischkewitzArmido Studer
Mar 25, 2017·Journal of the American Chemical Society·Emma K EdelsteinJames P Morken
Apr 13, 2017·Journal of the American Chemical Society·Mattia SilviVarinder K Aggarwal
Apr 14, 2017·Journal of the American Chemical Society·Surendra ThapaRamesh Giri
May 11, 2017·Journal of the American Chemical Society·Andrés García-DomínguezCristina Nevado
May 20, 2017·Angewandte Chemie·Beatrice S L CollinsVarinder K Aggarwal
Jul 25, 2017·Journal of the American Chemical Society·Joseph DerosaKeary M Engle
Jul 26, 2017·Angewandte Chemie·Matteo ChierchiaJames P Morken
Nov 9, 2017·Journal of the American Chemical Society·Gabriel J Lovinger, James P Morken
Feb 10, 2018·Journal of the American Chemical Society·Yang Xiong, Guozhu Zhang

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Citations

Dec 6, 2019·Chemical Communications : Chem Comm·Nivesh KumarAhmad Masarwa
Jan 8, 2020·Angewandte Chemie·Shang-Zheng SunRuben Martin
Mar 7, 2020·Chemistry : a European Journal·Ahmad MasarwaAlexander Shames
May 28, 2020·Organic & Biomolecular Chemistry·Huiyong YangWanmei Li
Jul 3, 2020·Advanced Synthesis & Catalysis·Marvin KischkewitzArmido Studer
Jul 8, 2020·Angewandte Chemie·Songlin ZhengWeiming Yuan
Oct 13, 2020·European Journal of Organic Chemistry·Gabriel J Lovinger, James P Morken
Mar 5, 2021·Journal of the American Chemical Society·Mark W CampbellGary A Molander
Aug 13, 2021·Accounts of Chemical Research·Laura M Wickham, Ramesh Giri
Aug 13, 2021·Journal of the American Chemical Society·Jin-Bao QiaoXing-Zhong Shu
Dec 4, 2020·Journal of the American Chemical Society·Roshan K DhunganaRamesh Giri
Aug 25, 2021·Journal of the American Chemical Society·Chenlong ZhangJames P Morken
Jul 1, 2020·Journal of the American Chemical Society·Xiaofeng WeiCristina Nevado
Mar 19, 2021·ACS Catalysis·Xiaoxu Qi, Tianning Diao
Aug 28, 2020·Journal of the American Chemical Society·Xianqing WuYifeng Chen
Nov 11, 2020·Journal of the American Chemical Society·Yue LiMengchun Ye
Nov 5, 2021·Journal of the American Chemical Society·Chao DingGuoyin Yin

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