- Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes
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Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.
- Hfaiedh, Anoir,Yuan, Kedong,Ben Ammar, Hamed,Ben Hassine, Bechir,Soulé, Jean-Fran?ois,Doucet, Henri
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p. 1794 - 1804
(2015/06/02)
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- Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans
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The reactivity of furan derivatives in palladium-catalyzed desulfitative arylation was studied. Alkyl-substituted furan derivatives were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst; regioselective arylation at C5 of the furan was observed in all cases. This reaction tolerates a wide variety of substituents on the benzenesulfonyl derivative. It should be noted that even bromo- and iodobenzenesulfonyl chlorides were successfully coupled with furan derivatives without cleavage of the C-Br or C-I bonds, thus allowing further transformations. The use of these reactants demonstrates the potential of benzenesulfonyl chlorides as coupling partners to access to functionalized 5-arylfurans.
- Beladhria, Anissa,Yuan, Kedong,Ben Ammar, Hamed,Soulé, Jean-Francois,Ben Salem, Ridha,Doucet, Henri
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p. 2515 - 2523
(2015/12/26)
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- Benzenesulfonyl chlorides: Alternative coupling partners for regiocontrolled palladium-catalyzed direct desulfitative 5-arylation of furans
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The reactivity of furan derivatives in palladium-catalyzed desulfitative arylation was studied. Alkyl-substituted furan derivatives were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst; regioselective arylation at C5 of the furan was observed in all cases. This reaction tolerates a wide variety of substituents on the benzenesulfonyl derivative. It should be noted that even bromo- and iodobenzenesulfonyl chlorides were successfully coupled with furan derivatives without cleavage of the C-Br or C-I bonds, thus allowing further transformations. The use of these reactants demonstrates the potential of benzenesulfonyl chlorides as coupling partners to access to functionalized 5-arylfurans.
- Beladhria, Anissa,Yuan, Kedong,Ben Ammar, Hamed,Soulé, Jean-Francois,Ben Salem, Ridha,Doucet, Henri
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p. 2515 - 2523
(2014/11/12)
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- Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: An economically and environmentally attractive access to 5-arylfurans
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The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)2 as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide ra
- Dong, Jia Jia,Roger, Julien,Pogan, Franc,Doucet, Henri
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experimental part
p. 1832 - 1846
(2011/03/18)
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