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Gold-catalyzed (5,5)-rearrangement

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 expe...

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Main Authors: Hu, Chao (Author) , Farshadfar, Kaveh (Author) , Dietl, Martin C. (Author) , Cervantes-Reyes, Alejandro (Author) , Wang, Tao (Author) , Adak, Tapas (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Li, Jun (Author) , Ariafard, Alireza (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 19 May 2021
In: ACS catalysis
Year: 2021, Volume: 11, Issue: 11, Pages: 6510-6518
ISSN:2155-5435
DOI:10.1021/acscatal.1c01108
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acscatal.1c01108
Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/acscatal.1c01108#
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Author Notes:Chao Hu, Kaveh Farshadfar, Martin C. Dietl, Alejandro Cervantes-Reyes, Tao Wang, Tapas Adak, Matthias Rudolph, Frank Rominger, Jun Li, Alireza Ariafard, and A. Stephen K. Hashmi
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Summary: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 Description:Published online 19 May 2021
Published in issue 4 June 2021
Gesehen am 02.08.2021
Physical Description:Online Resource
ISSN:2155-5435
DOI:10.1021/acscatal.1c01108

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