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DOI: 10.1055/s-2008-1078628
Directed Remote Metalation via N-Carbamoyl N Æ C Translocation
Contributor(s):Paul Knochel, Tobias ThalerQueen’s University, Kingston, Canada
Anionic Indole N-Carbamoyl N → C Translocation. A Directed Remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles
Org. Lett. 2008, 10: 2617-2620
Publication History
Publication Date:
22 August 2008 (online)
Key words
N-carbamoyl N Æ C translocation - directed remote metalation - 2-arylindoles - 2-heteroarylindoles
Significance
In this article a new directed remote metalation (DreM) concept is presented. Hereby, anionic N-carbamoyl migration was successfully used in the preparation of various 2-arylindoles. The carbamide functionality is directly and regioselectively transferred to the respective aryl or vinyl moiety.
Comment
This method in combination with the selective deprotonation of N-carbamoyl indoles at the C7 position
(Org. Lett. 2003, 5, 1899) is a powerful synthetic method
for the direct and straightforward construction of new complex
2,7-substituted
indoles containing carbamide moieties.
Review
On the complex-induced proximity effect (CIPE), including DreM: M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak Angew. Chem. Int. Ed. 2004, 43, 2206-2225.