Microwave-Promoted Copper-Free Sonogashira–Hagihara Couplings of Aryl Imidazolylsulfonates in Water

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Title: Microwave-Promoted Copper-Free Sonogashira–Hagihara Couplings of Aryl Imidazolylsulfonates in Water
Authors: Cívicos García, José Francisco | Alonso, Diego A. | Nájera, Carmen
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Cross-coupling | Microwave chemistry | Palladacycles | Sonogashira–Hagihara reaction | Water
Knowledge Area: Química Orgánica
Issue Date: 14-Jan-2013
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Advanced Synthesis & Catalysis. 2013, 355(1): 203-208. doi:10.1002/adsc.201200629
Abstract: Aryl imidazol-1-ylsulfonates have been efficiently cross-coupled with aryl-, alkyl-, and silylacetylenes in neat water under copper-free conditions at 110 °C assisted by microwave irradiation. Using 0.5 mol% of an oxime palladacycle as precatalyst, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 2 mol%) as ligand, hexadecyltrimethylammonium bromide (CTAB) as additive, and triethylamine (TEA) as base, a wide array of disubstituted alkynes has been prepared in good to high yields in only 30 min.
Sponsor: Financial support from the MICINN (Projects CTQ2007-62771/BQU, CTQ2010-20387 and Consolider INGENIO 2010 CSD2007-00006), FEDER, from the Generalitat Valenciana (Project PROMETEO/2009/038), and the University of Alicante is acknowledged.
URI: http://hdl.handle.net/10045/38196
ISSN: 1615-4150 (Print) | 1615-4169 (Online)
DOI: 10.1002/adsc.201200629
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/adsc.201200629
Appears in Collections:INV - CESO - Artículos de Revistas
INV - SINTAS - Artículos de Revistas

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