Journal
ORGANIC LETTERS
Volume 17, Issue 5, Pages 1252-1255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00235
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Funding
- Herbert C. Brown Center for Borane Research
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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)-beta-trifluoromethylstyrenes. Also, a safe synthesis of the alkynyltrifluoroborate from HFC-245fa and BF3 center dot OEt2 has been described.
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