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One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

Derek A. Leas, Yuxiang Dong, Jonathan L. Vennerstrom and Douglas E. Stack*

*Department of Pharmaceutical Sciences, College of Pharmacy, University of Nebraska Medical Center, Omaha, Nebraska 68198-6125, United States, Email: dstackunomaha.edu

D. A. Leas, Y. Dong, J. L. Vennerstrom, D. E. Stack, Org. Lett., 2017, 19, 2518-2521.

DOI: 10.1021/acs.orglett.7b00771 (free Supporting Information)


Abstract

Halogen abstraction from bromotrichloromethane and diiodomethane enables a metal-free synthesis of aryl bromides and iodides from anilines without isolation of diazonium salts. The transformation offers short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. This method represents a convenient alternative to the classic Sandmeyer reaction.

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Key Words

Sandmeyer reaction, aryl iodides, aryl bromides


ID: J54-Y2017