Gold(I)-Catalyzed Intramolecular C(sp3 )-H Insertion by Decarbenation of Cycloheptatrienes.

Xiang YinGiuseppe Zuccarello Cristina García-Morales Antonio M Echavarren

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)

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-center concerted mechanism for the C(sp3 )-H functionalization process.

Keyphrases

density functional theory
silver nanoparticles
molecular dynamics
molecular dynamics simulations
high resolution
crystal structure