Back to Search
Start Over
Cobalt-Catalyzed Regioselective Carbocyclization Reaction of o-Iodophenyl Ketones and Aldehydes with Alkynes, Acrylates, and Acrylonitrile: A Facile Route to Indenols and Indenes.
- Source :
-
Journal of Organic Chemistry . 7/9/2004, Vol. 69 Issue 14, p4781-4787. 7p. 2 Charts. - Publication Year :
- 2004
-
Abstract
- An efficient cobalt-catalyzed carbocylization for the synthesis of indenols and indenes and a new method for reductive decyanation are described. 2-Iodophenyl ketones and aldehydes la-g undergo carbocyclization with various disubstituted alkynes 2a-k in the presence of Co(dppe)I2 and zinc powder in acetonitrile at 80 °C for 3 h to afford the corresponding indenol derivatives 3a-s and 4a-m in good to excellent yields. For some unsymmetrical alkynes, the carbocyclization was remarkably regioselective, affording a single regioisomer. The cobalt-catalyzed carbocyclization reaction was successfully extended to the synthesis of indene derivatives. Thus, the reaction of 2-iodophenyl ketones and aldehydes (1) with acrylates H2C=CHCO2R (7a-d) and acrylonitrile H2C= CHCN (7e) proceeds smoothly in the presence of Co(dppe)Cl2/dppe and zinc powder in acetonitrile at 80 °C for 24 h to afford the corresponding indenes 8a-k and 9a-c in moderate to good yields. Interestingly, when 7e was employed for the carbocylization, reductive decyanation also occurred to give an indene derivative without the cyano functionality. A possible mechanism for this cobalt-catalyzed carbocyclization reaction is also proposed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 69
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 13863495
- Full Text :
- https://doi.org/10.1021/jo049506g