Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans
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
p. 2515 - 2523
(2015/12/26)
Benzenesulfonyl chlorides: Alternative coupling partners for regiocontrolled palladium-catalyzed direct desulfitative 5-arylation of furans
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
p. 2515 - 2523
(2014/11/12)
Synthesis of tetrasubstituted furans by palladium-catalyzed decarboxylative [3+2] cyclization of propargyl β-keto esters
The decarboxylative [3+2] cyclization reaction of propargyl β-keto esters with a palladium catalyst is described. Tetrasubstituted furans with a variety of substituents were conveniently synthesized with high efficiency (see scheme). Copyright
Yoshida, Masahiro,Ohno, Shoko,Shishido, Kozo
supporting information; experimental part
p. 1604 - 1607
(2012/03/10)
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