A Reaction Mechanism for Gold-Catalyzed Hydroamination/Cyclization of o‑Phenylendiamine and Propargylic Alcohols. A DFT Study
2018-09-12T15:21:55Z (GMT) by
The 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.
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