Intermolecular C(sp3 )-H Amination of Complex Molecules

Angewandte Chemie
Nicholas D ChiappiniJustin Du Bois

Abstract

A general and operationally convenient method for intermolecular amination of C(sp3 )-H bonds is described. This technology allows for efficient functionalization of complex molecules, including numerous pharmaceutical targets. The combination of pivalonitrile as a solvent, Al2 O3 as an additive, and phenyl sulfamate as a nitrogen source affords differential reaction performance and substrate scope. Mechanistic data strongly implicate a pathway for catalyst decomposition that initiates with solvent oxidation, thus providing rationale for the marked influence of pivalonitrile on this reaction process.

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Citations

Jan 25, 2019·Angewandte Chemie·Abolghasem Gus BakhodaTimothy H Warren
Apr 11, 2019·Angewandte Chemie·Ali NasrallahPhilippe Dauban
Mar 20, 2019·Angewandte Chemie·Alexandra E Bosnidou, Kilian Muñiz
Oct 21, 2020·Angewandte Chemie·Zhong-Wei HouHai-Chao Xu
Jan 23, 2021·Angewandte Chemie·Alexander FawcettJohn F Hartwig
Jun 29, 2021·Journal of the American Chemical Society·Alexander FanourakisRobert J Phipps
Sep 11, 2020·Journal of the American Chemical Society·Wei Pin TehForrest E Michael
Dec 25, 2019·Organic Letters·Kerry N BetzJ Du Bois
Apr 21, 2020·Journal of the American Chemical Society·Yeongyu HwangSukbok Chang
Oct 20, 2018·The Journal of Organic Chemistry·Anna TombergPer-Ola Norrby
Jun 4, 2020·ACS Central Science·Benke HongXiaoguang Lei
Jan 3, 2019·Journal of the American Chemical Society·James B C MackJ Du Bois
Jul 31, 2021·Angewandte Chemie·Yanis LazibPhilippe Dauban
Sep 25, 2019·Journal of the American Chemical Society·Anuvab DasDavid C Powers
Sep 7, 2018·Journal of the American Chemical Society·M Christina White, Jinpeng Zhao
May 1, 2018·The Journal of Organic Chemistry·Justin Y SuJ Du Bois
Sep 1, 2021·Journal of the American Chemical Society·Si-Jie ChenShannon S Stahl
Sep 14, 2021·Journal of the American Chemical Society·Takafumi IdeM Christina White
Sep 23, 2021·Journal of the American Chemical Society·J Henry BlackwellMatthew J Gaunt
Oct 2, 2021·Chemical Communications : Chem Comm·Ranjan JanaEnakshi Dinda
Oct 7, 2021·Journal of the American Chemical Society·Kelly E KimBrian M Stoltz

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