Synthesis of Indenes and Indanes by Gold(I)-Catalyzed Decarbenation

Identifier:  TDX:2885

Handle: https://hdl.handle.net/20.500.11797/TDX2885

Authors:  Yin, Xiang

Abstract:
7-substituted 1,3,5-cycloheptatrienes derivatives react with cationic gold(I) catalysts gave gold(I) carbenes by a retro-Buchner reaction in which two C-C bonds in norcaradienes are cleaved by Au(I). This novel strategy obviates the use of shock-sensitive diazo derivatives and generates reactive metal carbenes in situ which can undergo further diverse transformations, such as cyclopropanation of external and tethered alkenes and intramolecular Friedel-Crafts-type reactions. To broaden the range of synthetic methods and applications available for these useful intermediates, in the present Doctoral Thesis we have developed new gold(I)-carbenes induced transformations leading to the rapid construction of important frameworks and studied the mechanism experimentally and by DFT calculations.