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Computational Mechanistic Study of Fused Phenol Formations from 1,6‐Heptadiyne Involving Carbyne Complexes

Yamamoto, Yoshihiko 名古屋大学

2021.12.07

概要

The reaction of a tungsten carbyne complex, MeC≡WBr(CO)4, with 1,6-heptadiyne was investigated using density functional theory (DFT) calculations. It was suggested that the plausible mechanism involves [2+2] cycloaddition of the carbyne with the diyne, subsequent insertion of CO and alkyne into a metallacyclobutadiene intermediate, and a final reductive elimination step from a metallacycloheptatrienone intermediate to produce a η^5-cyclohexadienyl complex. A related Ru-catalyzed reaction of 1,6-heptadiyne involving a hydroxycarbyne complex was investigated to propose a possible pathway starting from a bis(hydroxycarbyne) complex, (HOC≡)2Ru(CO)2. It was found that the biscarbyne complex undergoes carbyne-carbyne coupling to generate a stable metallacyclopropene intermediate, which reacts with 1,6-heptadiyne through two different pathways to produce the final η^6-arene complex. Moreover, a non-carbyne pathway was also investigated to propose an alternative mechanism.

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