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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| Hauptverfasser: | , , , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
19 May 2021
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| In: |
ACS catalysis
Year: 2021, Jahrgang: 11, Heft: 11, Pages: 6510-6518 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.1c01108 |
| Online-Zugang: | 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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| Verfasserangaben: | 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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| 520 | |a 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. | ||
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