Hypervalent Iodine(III)-Catalysis Using Sulfoxide Oxidant for the Dehydrogenative Cycloisomerization-Arylation Reaction of 2-Propargyl 1,3-Dicarbonyl Compounds

被引:2
作者
Umakoshi, Yuki [1 ]
Tsubouchi, Akira [1 ]
Yoshimura, Akira [2 ]
Saito, Akio [1 ]
机构
[1] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, Koganei, Tokyo 1848588, Japan
[2] Aomori Univ, Fac Pharmaceut Sci, 2-3-1 Kobata, Aomori 0300943, Japan
关键词
arylation; cycloisomerization; iodine; sulfoxide; organocatalysis; METAL-FREE SYNTHESIS; METHYL KETONES; SUBSTITUTED QUINOLINES; UNPROTECTED ANILINES; C-O; ACTIVATION; INDOLES; SALTS; SPIROCYCLIZATION; DERIVATIVES;
D O I
10.1002/ejoc.202301241
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein an unprecedented hypervalent iodine(III)-catalysis using the activated sulfoxide. Since the present catalytic systems promote the dehydrogenative cycloisomerization-arylation reaction of 2-propargyl 1,3-dicarbonyl compounds with aromatics, this report also provides one of the few methods for iodine(III)-catalyzed intermolecular carbon-carbon bond formation of aromatics. Hypervalent iodine(III) catalysis using an activated sulfoxide as a terminal oxidant has been developed for the metal-free synthesis of arylated furans. o-Nitrobenzenesulfonyl chloride (o-NsCl) or the generated acid activates the sulfoxide. 1-(Chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium 4-methylbenzenesulfonate (TEDA-OTs) contributes to the stability of the activated sulfoxide. image
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页数:6
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