Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

Under palladium catalysis, Et3B nicely promotes allyl alcohols to undergo C3-selective allylation of indoles and tryptophan; the yields range 75-95%.

Pd(0)-catalyzed amphiphilic activation of bis-allyl alcohol and ether.

Pd(0).Et3B catalyzes amphiphilic activation of symmetric allylic diol 1 to promote electrophilic allylation at the alpha-position of aldehydes and nucleophilic allylation at the aldehyde CO, furnishing 3-methylenecyclopentalols 2 and thus generation of a zwitterionic trimethylenemethane species from the commercially available diol 1.