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(Z)- Or (E)-Selective Hydrogenation of Potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: Route to Either Isomer of β-trifluoromethylstyrenes

(Z)- Or (E)-Selective Hydrogenation of Potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: Route to Either Isomer of β-trifluoromethylstyrenes

P Veeraraghavan Ramachandran, Wataru Mitsuhashi

Org Lett. 2015 Mar 6;17(5):1252-5.

PMID: 25705923

Abstract:

A Pd-catalyzed hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate providing either the (Z)- or (E)-isomer of the vinylborate in >98% purity is described. The initially formed (Z)-isomer of the alkene is transformed to the (E)-isomer with time, irrespective of the catalyst used; coupling with bromo- and iodoarenes provides a variety of (Z)- or (E)-β-trifluoromethylstyrenes. Also, a safe synthesis of the alkynyltrifluoroborate from HFC-245fa and BF3·OEt2 has been described.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1268340937	(Piperidinium-1-ylmethyl)trifluoroborate		1268340-93-7	Price
AP910251104	Potassium (tert-butoxymethyl)trifluoroborate		910251-10-4	Price

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