Ligand-Enabled Nickel-Catalyzed Redox-Relay Migratory Hydroarylation of Alkenes with Arylborons

Angewandte Chemie
Yuli HeShaolin Zhu

Abstract

A redox-relay migratory hydroarylation of isomeric mixtures of olefins with arylboronic acids catalyzed by nickel complexes bearing diamine ligands is described. A range of structurally diverse 1,1-diarylalkanes, including those containing a 1,1-diarylated quaternary carbon, were obtained in excellent yields and with high regioselectivity. Preliminary experimental evidence supports the proposed non-dissociated chainwalking of aryl-nickel(II)-hydride species along the alkyl chain of alkenes before selective reductive elimination at a benzylic position. A catalyst loading as low as 0.5 mol % proved to be sufficient in large-scale synthesis while retaining high reactivity, highlighting the practical value of this transformation.

References

Jun 9, 1998·Drugs·C J HillsJ A Balfour
Jul 24, 1998·Carbohydrate Research·T AreeH Hoier
Dec 2, 1999·Journal of Natural Products·D H SilvaM Yoshida
May 5, 2001·Expert Opinion on Pharmacotherapy·A L McRae, K T Brady
Feb 11, 2004·Organic & Biomolecular Chemistry·W Russell BowmanMark B Schilling
Oct 30, 2007·Journal of the American Chemical Society·Keith M GligorichMatthew S Sigman
Jul 12, 2008·Chemical Reviews·Carl Deutsch, Norbert Krause
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Jul 12, 2011·Tetrahedron·Susanne M PodhajskyMatthew S Sigman
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 25, 2012·Journal of the American Chemical Society·Takuya KochiFumitoshi Kakiuchi
Apr 11, 2014·Nature·Tian-Sheng MeiMatthew S Sigman
May 16, 2014·Nature·Sarah Z TaskerTimothy F Jamison
Jun 6, 2014·Chemical Communications : Chem Comm·Evgeny LarionovClément Mazet
Aug 30, 2014·Journal of the American Chemical Society·Joseph S BairJohn F Hartwig
Nov 15, 2014·Journal of the American Chemical Society·Evgeny LarionovClément Mazet
May 27, 2015·Organic Letters·Margaret L ScheuermannPaul J Chirik
Oct 3, 2015·Angewandte Chemie·Ivan BuslovXile Hu
Feb 20, 2016·Nature Chemistry·Alexandre VasseurIlan Marek
Jun 28, 2016·Journal of the American Chemical Society·Stig D FriisStephen L Buchwald
Jul 20, 2016·Journal of the American Chemical Society·Luqing LinClément Mazet
Jul 21, 2016·Chemical Reviews·Nathan A Eberhardt, Hairong Guan
Jul 28, 2016·Chemical Reviews·Steven W M CrossleyRyan A Shenvi
Sep 14, 2016·Journal of the American Chemical Society·Samantha A GreenRyan A Shenvi
Oct 27, 2016·Angewandte Chemie·Stéphanie DupuyOlivier Baudoin
May 5, 2017·Nature·Francisco Juliá-HernándezRuben Martin
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Aug 18, 2017·Journal of the American Chemical Society·Morgane GaydouRuben Martin
Sep 8, 2017·Journal of the American Chemical Society·Fenglin ChenShaolin Zhu
Feb 21, 2018·Nature Chemistry·Daniel G KohlerKami L Hull

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Citations

May 13, 2021·Chemical Communications : Chem Comm·Yuanyuan HuBingwei Zhou
Jun 8, 2021·Chemical Science·Yangyang LiGuoyin Yin
Jun 22, 2021·Journal of the American Chemical Society·Chen-Fei LiuMing Joo Koh
May 8, 2020·Journal of the American Chemical Society·Alena M VasquezKeary M Engle
Nov 24, 2020·Organic Letters·Chenchen WangYifeng Chen
Nov 5, 2020·Organic Letters·Qi Cheng, Yanfeng Dang
Oct 1, 2020·Journal of the American Chemical Society·Xiaolong YuMing Joo Koh
Aug 27, 2021·Journal of the American Chemical Society·Jian Chen, Shaolin Zhu
Oct 7, 2021·Chemical Communications : Chem Comm·Soumen GhoshIndranil Chatterjee

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