Formal Insertion of a Metal Carbene Complex into a σ‐Carbon‐Carbon Bond. Gold‐Catalyzed Synthesis of 3 H ‐Indoles
We report here a formal insertion of a metal carbene complex in a single carbon‐carbon bond. This behavior occurs with the participation of an α‐imino gold carbene complex, generated from benzofused triazapentalenes or, in a one‐pot procedure, from their 1‐propargyl‐1 H ‐benzotriazole precursors, an...
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| Published in: | Advanced synthesis & catalysis Vol. 366; no. 9; pp. 1989 - 1995 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
21-05-2024
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| Online Access: | Get full text |
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| Summary: | We report here a formal insertion of a metal carbene complex in a single carbon‐carbon bond. This behavior occurs with the participation of an α‐imino gold carbene complex, generated from benzofused triazapentalenes or, in a one‐pot procedure, from their 1‐propargyl‐1
H
‐benzotriazole precursors, and gold‐catalytically activated ynamides. As the result, 3
H
‐indole derivatives were obtained, with formation of a quaternary center. A computational analysis carried out on the reaction mechanism indicates that the bulkiness of the gold ligand plays a key role forcing a conformation, which includes aromatic interactions, that favors the approximation of the carbenic carbon to the reactive site. In addition, a negative crossover experiment rules out a cationic arene migration pathway. |
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| ISSN: | 1615-4150 1615-4169 |
| DOI: | 10.1002/adsc.202400252 |