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A Reaction Mechanism for Gold-Catalyzed Hydroamination/Cyclization of o‑Phenylendiamine and Propargylic Alcohols. A DFT Study
journal contribution
posted on 2018-09-12, 15:21 authored by Yueyue Wang, Baoping Ling, Peng Liu, Siwei BiThe atom-economic gold-catalyzed
reaction of o-phenylendiamine and propargylic alcohols
was investigated theoretically
and computationally. A reaction mechanism was proposed with reasonable
energetics. The Au(I)-induced coupling of the two substrates allows
for the formation of a C–N bond, from which the reaction initiates
the dehydration by using the hydroxyl and the proton from the NH2+ moiety. Then cyclization is followed to give
a seven-membered ring species. Subsequently, 1,3-proton transfer,
Au–C bond cleavage, C–H bond formation, and deprotonation
evolve into the product.