Rhodium-catalysed Cyclisation Reaction Of Allenynes With Arylboronic Acids

摘要

Allenynes having malonate-based tethers reacted with arylboronic acids in the presence of a rhodium(I) catalyst to sequentially form three carbon-carbon bonds, and arylated bicyclic skeletons were constructed in a stereoselective manner.rnRecently, the rhodium-catalysed cyclisation reaction with organoboron reagents has been demonstrated to be a powerful method for the synthesis of carbocyclic compounds. An organorhodium(I) species, generated through transmetalation between rhodium(I) and boron, can undergo multiple carbo-rhodation steps onto acceptor compounds bearing two and more functional groups to form cyclic skeletons. An alkyne moiety provides an expedient entry point for incorporation of an organorhodium(I) species in the molecule, which then adds intramolecularly to another functional group. We have previously described the rhodium-catalysed cyclisation reaction of 1,6-enynes with arylboronic acids to form arylated bicyclic compounds with a stereodefined exocyclic double bond.