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Functionalization of Unactivated Alkenes through Iridium-Catalyzed Borylation of Carbon-Hydrogen Bonds. Mechanism and Synthetic Applications

Vilhelm J. Olsson and Kálmán J. Szabó*

*Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden, Email: kalmanorgan.su.se

V. J. Olsson, K. J. Szabó, J. Org. Chem., 2009, 74, 7715-7723.

DOI: 10.1021/jo9014694 (free Supporting Information)


Abstract

In situ generation of allylic boronates by iridium-catalyzed borylation of cyclic alkenes in the presence of additives, such as methylimidazole and DBU, followed a reaction with aldehydes allows the synthesis of stereodefined homoallylic alcohols. Cycloalkenes without additives as well as acyclic substrates gave vinylic boronates, which were coupled with organohalides in a Suzuki-Miyaura sequence.


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Key Words

cyclopentenes, cyclohexenes, cycloheptenes, vinylboronates, allylboronates, homoallylic alcohols, Suzuki Coupling


ID: J42-Y2009-2900