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Transition-Metal-Free Sonogashira-Type Coupling of ortho-Substituted Aryl and Alkynyl Grignard Reagents by Using 2,2,6,6-Tetramethylpiperidine-N-oxyl Radical as an Oxidant

Modhu Sudan Maji, Sandip Murarka and Armido Studer*

*Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraβe 40, 48149 Münster, Germany, Email: studeruni-muenster.de

M. S. Maji, S. Murarka, A. Studer, Org. Lett., 2010, 12, 3878-3881.

DOI: 10.1021/ol1015702 (free Supporting Information)


Abstract

Cross coupling of ortho-substituted aryl Grignard reagents with alkynyl Grignard reagents can be performed without adding any transition metal in the presence of 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) as an environmentally benign organic oxidant. Importantly, functional groups such as esters, amides, and cyanides are tolerated.

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Key Words

Akynylation, Green Chemistry, TEMPO


ID: J54-Y2010-2500