Rh(III)-Catalyzed Tandem C-H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles
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American Chemical Society
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Abstract
RhIII-catalyzed tandem C-H allylation and oxidative cyclization of anilides with allyl carbonates in the presence of a slight excess of AgSbF6 salt and Cu(OAc)2 as oxidant affords easy, economical access to important bioactive 2-methylindoles. The new reaction supports a wide range of functional groups on the anilide substrate. A possible mechanism is proposed as a basis for its rational further development.
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NOTICE: This is the peer reviewed version of the following article: Cajaraville, A., López, S., Varela, J. A., Saá, C. (2013). Rh(III)-Catalyzed Tandem C-H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles. Org. Lett., 15, 17, 4576-4579. [doi: 10.1021/ol402125t]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
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Cajaraville, A., López, S., Varela, J. A., Saá, C. (2013). Rh(III)-Catalyzed Tandem C-H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles. Org. Lett., 15, 17, 4576-4579
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https://doi.org/10.1021/ol402125tSponsors
This work was supported by MICINN [projects CTQ2011-28258 and Consolider Ingenio 2010 (CSD2007-00006)] and Xunta de Galicia (projects CN2011/054 and EM 2012/051). We thank M. J. Cotón for preliminary experiments. A.C. thanks Ministerio de Ciencia e Innovación for a FPI predoctoral fellowship
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Copyright © 2013 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving