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Pd-Catalyzed Regio- and Stereoselective Addition of Boronic Acids to Silylacetylenes: A Stereodivergent Assembly of β,β-Disubstituted Alkenylsilanes and Alkenyl Halides

Wei Kong, Chao Che, Jialin Wu, Liai Ma and Gangguo Zhu*

*Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China, Email: gangguozjnu.cn

W. Kong, C. Che, J. Wu, L. Ma, G. Zhu, J. Org. Chem., 2014, 79, 5799-5805.

DOI: 10.1021/jo500925p (free Supporting Information)



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Abstract

An efficient Pd-catalyzed addition of boronic acids to silylacetylenes provides β,β-disubstituted (E)- or (Z)-alkenylsilanes in good yields with excellent regio- and stereoselectivity under mild reaction conditions. Moreover, a sequential Pd-catalyzed boron addition/N-halosuccinimide-mediated halodesilylation reaction results in a stereodivergent approach to β,β-disubstituted alkenyl halides as versatile synthetic intermediates.

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Key Words

arylation, vinyl silanes


ID: J42-Y2014