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Regio- and Stereoselective Allylation and Crotylation of Indoles at C2 Through the Use of Potassium Organotrifluoroborate Salts


  • The Natural Science and Engineering Research Council (NSERC) of Canada supported this work.


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A practical method for the allylation, prenylation, propargylation, and diastereoselective crotylation of indoles has been developed using air- and moisture-stable potassium organotrifluoroborate reagents (see scheme). Lewis acids such as BF3⋅Et2O promote addition to afford 2-allyl- and 2-crotylindolines in high yields and diastereoselectivities.