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Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

Daniel R. Fandrick*, Keith R. Fandrick, Jonathan T. Reeves, Zhulin Tan, Courtney S. Johnson, Heewon Lee, Jinhua J. Song, Nathan K. Yee and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email:

D. R. Fandrick, K. R. Fandrick, J. T. Reeves, Z. Tan, C. S. Johnson, H. Lee, J. J. Song, N. K. Yee, C. H. Senanayake, Org. Lett., 2010, 12, 88-91.

DOI: 10.1021/ol902457m

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A propargylation of aldehydes and ketones with allenyl and propargyl boronates is mediated by a catalytic amount of zinc. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

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Key Words

Homopropargylic Alcohols

ID: J54-Y2010-0110