Trifluoromethoxylation of Arenes: Synthesis of  ortho ‐Trifluoromethoxylated Aniline Derivatives by OCF 3  Migration | Zendy

Hojczyk Katarzy. | Zendy; Feng Pengju | Zendy; Zhan Chengbo | Zendy; Ngai MingYu | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Trifluoromethoxylation of Arenes: Synthesis of ortho ‐Trifluoromethoxylated Aniline Derivatives by OCF 3 Migration

Author(s) -

Hojczyk Katarzy.,

Feng Pengju,

Zhan Chengbo,

Ngai MingYu

Publication year - 2014

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.201409375

Subject(s) - aniline , hydroxylamine , heterolysis , reagent , aryl , chemistry , intramolecular force , functional group , combinatorial chemistry , trifluoromethylation , organic chemistry , trifluoromethyl , catalysis , alkyl , polymer

Aryl trifluoromethoxylation by a two‐step sequence of O‐trifluoromethylation of N‐aryl‐N‐hydroxylamine derivatives and intramolecular OCF 3 migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho‐OCF 3 aniline derivatives. In addition, it utilizes bench‐stable reagents, is operationally simple, shows high functional‐group tolerance, and is amenable to gram‐scale as well as one‐pot synthesis. A reaction mechanism of a heterolytic cleavage of the NOCF 3 bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF 3 ‐migration reaction.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research