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Abstract

A highly efficient gold-catalyzed cycloisomerization of 1,5-diynes was developed. Various functional groups are tolerated under the mild reaction conditions, which provides an alternative approach for the synthesis of indeno[1,2-c]furans. On the basis of mechanistic studies, including crossover experiments, deuterium labeling, and computational chemistry, the product formation proceeds via a formal [5,5]-sigmatropic rearrangement, a yet unknown reactivity pattern in gold catalysis. Instead of a synchronous concerted [5,5]-sigmatropic rearrangement and beyond an asynchronous concerted mode, each involving a single transition state, two energetically low transition states (1.8 and 5.6 kJ/mol) and an intermediate associate of the migrating benzyl cation and the vinyl gold species could be located in the computations.

Item Type:	Article
Authors/Creators:	Hu, C and Farshadfar, K and Dietl, MC and Cervantes-Reyes, A and Wang, T and Adak, T and Rudolph, M and Rominger, F and Li, J and Ariafard, A and Hashmi, ASK
Keywords:	gold catalysis, reaction mechanism, DFT calculations, rearrangement
Journal or Publication Title:	ACS Catalysis
Publisher:	American Chemical Society
ISSN:	2155-5435
DOI / ID Number:	https://doi.org/10.1021/acscatal.1c01108
Copyright Information:	© 2021 American Chemical Society
Related URLs:	Google Scholar: Ariafard, A UTAS Profile: Ariafard, A
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