Convenient Preparation of Cycloalkenyl Boronic Acid Pinacol Esters
A practical method for the preparation of cycloalkenyl boronic acid pinacol esters is described. These important synthetic intermediates are typically made using more expensive methods like transition metal-catalyzed borylation of alkenyl halides or triflates. In this work, they are obtained from the simple corresponding cycloalkanones, which are subjected to Shapiro reaction conditions followed by trapping with a borate ester. The requisite products are obtained in very good to excellent yields, and the reactions can be scaled up to multigram amounts. By providing a simple alternative to common methods that make use of expensive transition-metal catalysts and formation of sensitive intermediates, this convenient method will be useful for the synthesis of ring-containing partners for Suzuki-Miyaura cross-coupling and other reactions employing boronic esters as substrates.
Keywords: Boronic acid; Shapiro reaction; Suzuki-Miyaura cross-coupling; boronic esters
Document Type: Research Article
Affiliations: Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada
Publication date: 01 January 2008
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