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Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions

Scott E. Denmark and Zhigang Wang

*Department of Chemistry, 245 Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, Email:

S. E. Denmark, Z. Wang, Org. Lett., 2001, 3, 933-935.

DOI: 10.1021/ol0156751 (free Supporting Information)

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The combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling enables a formal hydrocarbation of terminal alkynes. The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane achieved excellent regio- and stereoselectivity. The cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.

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Key Words

Hiyama Coupling, alkenylation

ID: J54-Y2001