Synfacts 2009(6): 0630-0630  
DOI: 10.1055/s-0029-1217151
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Cross-Coupling of Secondary Boronic Esters

Contributor(s): Mark Lautens, David A. Candito
D. Imao, B. W. Glasspoole, V. S. Laberge, C. M. Crudden*
Queen’s University, Kingston, Canada
Further Information

Publication History

Publication Date:
25 May 2009 (online)


The cross-coupling of secondary alkyl organoboron reagents with organohalides has been a significant challenge; consequently there are a limited number of reports in the current literature (e.g., H. Doucet Eur. J. Org. Chem. 2008, 2013). The authors report the palladium-catalyzed cross-coupling of secondary boronic esters with aryl halides proceeding with retention of configuration. This report significantly expands the scope of cross-coupling methodologies employing secondary organoboron reagents.