Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile: a facile route to indenols and indenes

The Journal of Organic Chemistry
Kuo-Jui ChangChien-Hong Cheng

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 1a-g undergo carbocyclization with various disubstituted alkynes 2a-k in the presence of Co(dppe)I(2) and zinc powder in acetonitrile at 80 degrees C for 3 h to afford the corresponding indenol derivatives 3a-s and4a-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 H(2)C=CHCO(2)R (7a-d) and acrylonitrile H(2)C=CHCN (7e) proceeds smoothly in the presence of Co(dppe)Cl(2)/dppe and zinc powder in acetonitrile at 80 degrees 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.

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Citations

Oct 22, 2008·Chemical Communications : Chem Comm·Muriel Amatore, Corinne Gosmini
Nov 8, 2011·Acta Crystallographica. Section E, Structure Reports Online·C John McAdamZheng Shi
Feb 22, 2012·Acta Crystallographica. Section E, Structure Reports Online·Lyall R HantonJim Simpson
Sep 2, 2008·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Hirokazu Tsukamoto
Jul 18, 2015·The Journal of Organic Chemistry·Dattatraya H DetheSourav Ghosh
Apr 26, 2016·Chemical Reviews·Vadim P BoyarskiyAleksander V Vasilyev
Mar 24, 2017·The Journal of Organic Chemistry·Anupam JanaKarol Grela
Jul 3, 2009·Journal of the American Chemical Society·Rebecca Keller Friedman, Tomislav Rovis
Oct 18, 2018·Chemical Communications : Chem Comm·Heena PanchalHon Wai Lam
Oct 24, 2018·Organic & Biomolecular Chemistry·Pierre Querard, Chao-Jun Li
May 25, 2012·Chemical Communications : Chem Comm·Kanniyappan ParthasarathyChien-Hong Cheng
Aug 2, 2013·Chemical Communications : Chem Comm·Dattatraya H Dethe, Ganesh M Murhade
May 8, 2010·Organic Letters·Benoit GourdetHon Wai Lam
Feb 13, 2010·Chemical Reviews·Gérard Cahiez, Alban Moyeux
Dec 4, 2008·Organic Letters·Zulfiqar Ali Khan, Thomas Wirth
Mar 25, 2009·The Journal of Organic Chemistry·Jeanne-Marie Bégouin, Corinne Gosmini
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Apr 10, 2015·Accounts of Chemical Research·Parthasarathy Gandeepan, Chien-Hong Cheng
Jan 17, 2020·The Journal of Organic Chemistry·Chang-Xue GuMing-Hua Xu
Nov 17, 2006·Organic Letters·Ying-Chieh WongChien-Hong Cheng
Sep 30, 2005·Journal of the American Chemical Society·Yoichiro KuninobuKazuhiko Takai

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