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Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides

Ling Li, Shibin Zhao, Amruta Joshi-Pangu, Mohamed Diane and Mark R. Biscoe*

*Department of Chemistry, The City College of New York (CCNY), 160 Convent Avenue, New York, New York 10031, United States, Email: mbiscoeccny.cuny.edu

L. Li, S. Zhao, A. Joshi-Pangu, M. Diane, M. R. Biscoe, J. Am. Chem. Soc., 2014, 136, 14027-14030.

DOI: 10.1021/ja508815w (free Supporting Information)



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Abstract

A Pd-catalyzed, stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration.

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Key Words

suzuki coupling, alkylation


ID: J48-Y2014