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. 2018 Apr 23;57(18):4956-4959.
doi: 10.1002/anie.201713225. Epub 2018 Mar 22.

Intermolecular C(sp3 )-H Amination of Complex Molecules

Nicholas D Chiappini  1 , James B C Mack  1 , J Du Bois  1
Affiliations

Intermolecular C(sp3 )-H Amination of Complex Molecules

Nicholas D Chiappini et al. Angew Chem Int Ed Engl. .

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.

Keywords: C−H oxidation; amination; reaction mechanisms; rhodium; sulfamates.

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