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 |
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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 |
Files in This Item:
File | Description | Size | Format | |
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2013_Civicos_etal_AdvSynthCatal_final.pdf | Versión final (acceso restringido) | 257,09 kB | Adobe PDF | Open Request a copy |
2013_Civicos_etal_AdvSynthCatal.pdf | Versión revisada (acceso abierto) | 310,65 kB | Adobe PDF | Open Preview |
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