Premium
Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp 3 )−H and C(sp 2 )−H under Rhodium(III) Catalysis
Author(s) -
Yu Songjie,
Tang Guodong,
Li Yingzi,
Zhou Xukai,
Lan Yu,
Li Xingwei
Publication year - 2016
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.201602224
Subject(s) - rhodium , nitrene , amination , nucleophile , bifunctional , chemistry , catalysis , reagent , aniline , electrophile , medicinal chemistry , stereochemistry , organic chemistry
Previous direct C−H nitrogenation suffered from simple amidation/amination with limited atom‐economy and is mostly limited to C(sp 2 )−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp 2 )−H and C(sp 3 )−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the resting state of the catalyst, and DFT studies established the intermediacy of a nitrene species.