ol902457m_si_002.pdf (16.62 MB)
Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates
journal contribution
posted on 2010-01-01, 00:00 authored by Daniel R. Fandrick, Keith R. Fandrick, Jonathan T. Reeves, Zhulin Tan, Courtney S. Johnson, Heewon Lee, Jinhua J. Song, Nathan K. Yee, Chris H. SenanayakeThe utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.