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Indolylborates, prepared in situ from 2-bithio-1-methylindol and triethyl borane, form indol-2-yl-ketones by palladium-catalyzed carbonylative cross-coupling reactions. These reactions are fast under carbon monoxide in THF with vinyltriflates at 60 degrees C. All reactions are done in a single vessel. Stereochemistries of the compounds are assigned by NOE studies.

The development of a new atom-economical In[(OTf).sub.3]-catalyzed synthesis of ring-condensed heteroaromatic compounds via a domino intramolecular nucleophilic attack/intermolecular cycloaddition/dehydration reaction is reported. The synthesis used readily available ortho-alkynylanilines and ortho-alkynylbenzaldehydes as starting materials.

Studies the palladium-catalyzed carbonylative cross-coupling reaction with triethyl(1-methylindol-2-yl)borate. Indolylborate intermediate; Transformation of borate; Ketone synthesis.

Concise and efficient syntheses of various trans-2,3-disubstituted-2,3-dihydro-4-quinolones have been achieved via tandem Hofmann-type rearrangement of 2-alkynylbenzamides, nucleophilic addition of alcohols to the isocyanate intermediates, intermolecular [2+2]-cycloaddition with carbon-carbon triple bonds and aldehydes, and intramolecular aminocyclization of nitrogen of carbamates to the α,β-unsaturated ketones.