protocol-for-synthesis-ortho-trifluoromethoxylated-aniline

Protocol for the Synthesis of <em>Ortho</em>-trifluoromethoxylated Aniline Derivatives

Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of ...

State University of New York at Stony Brook

A rapid approach to the skeleton of dalesconol A and B, unprecedented immunosuppressants, has been achieved through a convergent strategy featuring a carbocation-mediated dearomatization-cyclization and a following one-pot consecutive operation.

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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.

Pengju Feng

Department of Chemistry,
Institute of Chemical Biology and Drug Discovery

State University of New York at Stony Brook

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Pengju Feng

.css-o250i3{font-size:18px;font-family:Open Sans,sans-serif;line-height:21.6px;}Department of Chemistry,Institute of Chemical Biology and Drug Discovery

State University of New York at Stony Brook

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Department of Chemistry,
Institute of Chemical Biology and Drug Discovery