An Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction: Highly Efficient Method To Prepare Planar Chiral Ferrocenes

Journal of the American Chemical Society
De-Wei GaoShu-Li You

Abstract

A Pd-catalyzed, asymmetric oxidative cross-coupling reaction between ferrocenes and heteroarenes is described. The process, which takes place via a twofold C-H bond activation pathway, proceeds with modest to high efficiencies (36-86%) and high levels of regio- and enantioselectivity (95-99% ee). In the reaction, air oxygen serves as a green oxidant and excess amounts of the coupling partners are not required. The process is the first example of a catalytic asymmetric biaryl coupling reaction that occurs via double C-H bond activation. Finally, the generated coupling products can be readily transformed into chiral ligands and catalysts.

References

Nov 20, 2001·Chemical Reviews·L Pu, H B Yu
Jan 13, 2006·Angewandte Chemie·E Peter KündigGérald Bernardinelli
May 26, 2007·Science·David R Stuart, Keith Fagnou
Sep 12, 2007·Journal of the American Chemical Society·Kami L Hull, Melanie S Sanford
Sep 21, 2007·Journal of the American Chemical Society·David R StuartKeith Fagnou
May 10, 2008·Organic Letters·Gordon BrascheStephen L Buchwald
Apr 14, 2009·Journal of the American Chemical Society·Hiromichi Egami, Tsutomu Katsuki
Dec 19, 2009·Journal of the American Chemical Society·Bing-Feng ShiJin-Quan Yu
Jan 28, 2010·Journal of the American Chemical Society·Peihua XiJingsong You
Jan 30, 2010·Journal of the American Chemical Society·Masamichi OgasawaraTamotsu Takahashi
Jan 30, 2010·Chemical Society Reviews·James A Ashenhurst
Apr 3, 2010·Journal of the American Chemical Society·Xiaodan ZhaoVy M Dong
Aug 21, 2010·Angewandte Chemie·Alice RenaudatOlivier Baudoin
Sep 2, 2010·Journal of the American Chemical Society·Chun-Yang HeXingang Zhang
Sep 14, 2010·Journal of the American Chemical Society·Hiromichi EgamiTsutomu Katsuki
Dec 22, 2010·Organic Letters·Hu LiZhang-Jie Shi
Jan 5, 2011·Journal of the American Chemical Society·Didier G Pintori, Michael F Greaney
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Aug 13, 2011·Journal of the American Chemical Society·Xisheng WangJin-Quan Yu
Sep 20, 2011·Chemical Communications : Chem Comm·Saithalavi AnasHenri B Kagan
Nov 9, 2011·Journal of the American Chemical Society·Masayuki WasaJin-Quan Yu
Dec 20, 2011·Chemical Communications : Chem Comm·Nathalie DendeleChristopher J Richards
Jan 31, 2012·Angewandte Chemie·Joanna Wencel-DelordFrank Glorius
Mar 13, 2012·Chemistry : a European Journal·Nicolas MartinOlivier Baudoin
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius

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Citations

Jun 28, 2016·The Journal of Organic Chemistry·Takanori ShibataKyalo Stephen Kanyiva
Jan 14, 2017·Chemical Reviews·Yudong YangJingsong You
Jan 27, 2017·The Journal of Organic Chemistry·Vijayakumar KondapalliMing Bao
May 4, 2017·The Journal of Organic Chemistry·Shao-Bo WangShu-Li You
Aug 4, 2018·Organic & Biomolecular Chemistry·Maral Gholamhosseyni, Ebrahim Kianmehr
Aug 18, 2017·Angewandte Chemie·Jorge Otero-FragaAbraham Mendoza
Sep 6, 2018·Chemical Communications : Chem Comm·Qiao-Ying SunLi-Wen Xu
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Santhivardhana Reddy YetraLutz Ackermann
Jan 28, 2020·Chemical Communications : Chem Comm·Wei-Xin KongWei-Liang Duan
Sep 15, 2019·Nature Communications·Zhong-Jian CaiShu-Li You
Oct 30, 2016·Chemistry : a European Journal·Soufyan JerhaouiFrançoise Colobert
Feb 3, 2021·Journal of the American Chemical Society·Shao-Jie LouZhaomin Hou
Mar 14, 2021·Organic Letters·Zhuo-Zhuo ZhangBing-Feng Shi
Mar 30, 2021·Journal of the American Chemical Society·Rupert S J ProctorRobert J Phipps
Jun 23, 2021·Chemistry : a European Journal·Gao HuangChangduo Pan
Jan 27, 2019·Organic Letters·Dan-Ying HuangBing-Feng Shi
Aug 10, 2018·Journal of the American Chemical Society·Wei LiuM Christina White
Jul 26, 2019·The Journal of Organic Chemistry·Jia-Chen XiangShu-Li You
Nov 17, 2020·The Journal of Organic Chemistry·Raviraj Ananda ThoratSangit Kumar

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