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Gold-catalyzed [5,5]-rearrangement

Hu, C, Farshadfar, K, Dietl, MC, Cervantes-Reyes, A, Wang, T, Adak, T, Rudolph, M, Rominger, F, Li, J, Ariafard, A ORCID: 0000-0003-2383-6380 and Hashmi, ASK 2021 , 'Gold-catalyzed [5,5]-rearrangement' , ACS Catalysis, vol. 11, no. 11 , pp. 6510-6518 , doi: 10.1021/acscatal.1c01108.

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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: 10.1021/acscatal.1c01108
Copyright Information:

© 2021 American Chemical Society

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