Trifluoromethoxylation of Arenes: Synthesis of ortho‐Trifluoromethoxylated Aniline Derivatives by OCF3 Migration1. Issue 52 (30th October 2014)

• Record Type: Journal Article
• Authors: Hojczyk, Katarzyna N.; Feng, Pengju; Zhan, Chengbo; Ngai, Ming‐Yu
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 52(2014)
• Page Start: 14559
• Page End: 14563
• Publication Date: 2014-10-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201409375
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Aryl trifluoromethoxylation by a two‐step sequence of O‐trifluoromethylation of N‐aryl‐N‐hydroxylamine derivatives and intramolecular OCF₃ migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho‐OCF₃ 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 NOCF₃ bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF₃‐migration reaction.</p> </abstract>