A novel synthesis of indanes and dihydronaphtalenes based on the intramolecular insertion into C(sp3)H bonds of gold(I) carbenes generated by retro-Buchner reaction (decarbenation) has been developed. Deuterium-labeling and kinetic isotope effect experiments, DFT calculations, and generation of the proposed carbene intermediate from a well-characterized gold(I) carbenoid support the involvement of a three-centered concerted mechanism for the C(sp3)H functionalization process.
Gold(I)-Catalyzed Intramolecular C(sp3)H Insertion by Decarbenation of Cycloheptatrienes
Chem. Eur. J 2019, 25 (40), 9485-9490, DOI: 10.1002/chem.201900919.