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Intermolecular C(sp 3 )−H Amination of Complex Molecules
Author(s) -
Chiappini Nicholas D.,
Mack James B. C.,
Du Bois J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713225
Subject(s) - amination , intermolecular force , molecule , chemistry , solvent , catalysis , decomposition , substrate (aquarium) , combinatorial chemistry , organic chemistry , oceanography , geology
A general and operationally convenient method for intermolecular amination of C(sp 3 )−H bonds is described. This technology allows for efficient functionalization of complex molecules, including numerous pharmaceutical targets. The combination of pivalonitrile as a solvent, Al 2 O 3 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.