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Synlett 1996; 1996(9): 842-844
DOI: 10.1055/s-1996-5596
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Bis(2,2,2-trifluoroethyl)phosphate as a Leaving Group for Highly Regioselective Cross-Coupling Reactions of Allylic Alcohol Derivatives with Allylic Organometallics

Akira Yanagisawa, Katsutaka Yasue, Hisashi Yamamoto*
  • *Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan, Fax: 81-52-789-3222
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Publication Date:
31 December 2000 (online)

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Regioselective cross-coupling reaction of allylic alcohol derivatives with allylic metal reagents were achieved using bis(2,2,2-trifluoroethyl)phosphate as a leaving group. Reaction with allylic magnesium reagent resulted in α,γ’ cross-coupling, whereas α,α’ cross-coupling occurred with allylic barium reagent. When a 1:1 mixture of (E)-2-octenyl 1-bis(2,2,2-trifluoroethyl)phosphate and (E)-2-decenyl chloride was treated with 1 equiv of reactive barium, the cross-coupling products were obtained with 86% selectivity and an α,α’/α,γ’ ratio of 94/6.

Bis(2,2,2-trifluoroethyl)phosphate - Allylic Grignard reagent - Allylic barium reagent - Regioselective cross-coupling reaction