Synlett 2016; 27(03): 313-319
DOI: 10.1055/s-0035-1560516
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Trifluoromethoxylated (Hetero)Arenes via OCF3 Migration

Katarzyna N. Lee
a  Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, USA
b  Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York 11794-3400, USA   Email: ming-yu.ngai@stonybrook.edu
,
Johnny W. Lee
a  Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, USA
b  Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York 11794-3400, USA   Email: ming-yu.ngai@stonybrook.edu
,
Ming-Yu Ngai*
a  Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, USA
b  Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York 11794-3400, USA   Email: ming-yu.ngai@stonybrook.edu
› Author Affiliations
Further Information

Publication History

Received: 15 September 2015

Accepted: 02 October 2015

Publication Date:
16 November 2015 (online)

Abstract

Incorporation of the OCF3 group into organic molecules, especially aromatic and heteroaromatic compounds, is recognized as one of the major challenges in synthetic organic chemistry. Although many attempts have been made to develop efficient trifluoromethoxylation strategies, most of the current approaches still require use of highly toxic, thermally unstable reagents, or impractical reaction conditions. Herein, we highlight a recent contribution from our group towards the synthesis of (hetero)aryltrifluoromethyl ethers. Our protocol is scalable, operationally simple, and allows an easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives, as well as functionalized trifluoromethoxylated pyridines and pyrimidines under mild reaction conditions.

 
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