Iridium(iii)-bis(imidazolinyl)phenyl catalysts for enantioselective C-H functionalization with ethyl diazoacetate

Chemical Science
N Mace WeldySimon Blakey

Abstract

The intermolecular enantioselective C-H functionalization with acceptor-only metallocarbenes is reported using a new family of Ir(iii)-bis(imidazolinyl)phenyl catalysts, developed based on the interplay of experimental and computational insights. The reaction is tolerant of a variety of diazoacetate precursors and is found to be heavily influenced by the steric and electronic properties of the substrate. Phthalan and dihydrofuran derivatives are functionalized in good yields and excellent enantioselectivities.

References

May 16, 1997·The Journal of Organic Chemistry·Scott E. DenmarkJames P. Edwards
Feb 7, 2002·Journal of the American Chemical Society·M Mar Díaz-RequejoPedro J Pérez
Feb 19, 2002·Chemical Reviews·Michael P. Doyle, David C. Forbes
Aug 14, 2003·Chemical Reviews·Huw M L Davies, Rohan E J Beckwith
Apr 8, 2006·Science·Kamil Godula, Dalibor Sames
Jun 20, 2007·Chemical Society Reviews·Hisao Nishiyama
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Jul 22, 2008·Angewandte Chemie·Erika MilczekSimon Blakey
Jul 30, 2009·The Journal of Organic Chemistry·Jørn HansenHuw M L Davies
Oct 10, 2009·The Journal of Organic Chemistry·Matthew S Sigman, Jeremie J Miller
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Jul 10, 2010·Organic & Biomolecular Chemistry·Tom G Driver
Nov 23, 2010·Chemical Society Reviews·Hongjian Lu, X Peter Zhang
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Apr 24, 2012·Nature Chemistry·Kaid C HarperMatthew S Sigman
May 2, 2012·Accounts of Chemical Research·Jennifer L RoizenJ Du Bois
Jun 28, 2012·Chemistry : a European Journal·David Y-K Chen, So Won Youn
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Nov 29, 2013·Organic Letters·David M GuptillHuw M L Davies
Dec 5, 2014·Journal of the American Chemical Society·David M Guptill, Huw M L Davies
Jun 9, 2015·Chemical Society Reviews·Andrew G Schafer, Simon B Blakey
Nov 17, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Ana CaballeroPedro J Pérez

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Citations

May 16, 2019·Organic & Biomolecular Chemistry·Jin-Kui LiuMao-Ping Song
Apr 3, 2018·Advanced Synthesis & Catalysis·Gopeekrishnan SreenilayamRudi Fasan
Jun 1, 2019·Nature Reviews. Chemistry·Huw M L Davies, Kuangbiao Liao
Apr 14, 2017·Chemical Communications : Chem Comm·Shota AsaiYoshinari Sawama
Oct 29, 2020·Angewandte Chemie·Shutao SunLei Liu
Apr 23, 2021·Physical Chemistry Chemical Physics : PCCP·Reena BalharaGarima Jindal
Jul 24, 2021·Chemical Reviews·Yajie WangHuimin Zhao
Jun 13, 2019·Journal of the American Chemical Society·Juner ZhangFrances H Arnold
Jun 23, 2018·Journal of the American Chemical Society·Daniele MazzarellaPaolo Melchiorre
Sep 9, 2020·Chemical Reviews·Łukasz WoźniakNicolai Cramer
Jan 30, 2019·Accounts of Chemical Research·Sean N Natoli, John F Hartwig
Jan 16, 2018·Journal of the American Chemical Society·Daniel J TindallAlois Fürstner
Oct 6, 2017·ACS Central Science·Huw M L Davies, Daniel Morton
Nov 5, 2021·Chemical Communications : Chem Comm·Janis Mikelis ZakisJoanna Wencel-Delord

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