Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp 3 )−H and C(sp 2 )−H under Rhodium(III) Catalysis | Zendy

Yu Songjie | Zendy; Tang Guodong | Zendy; Li Yingzi | Zendy; Zhou Xukai | Zendy; Lan Yu | Zendy; Li Xingwei | Zendy

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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.

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