One-Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium - Dihydroxyterphenylphosphine Catalyst

被引：37
|
作者：
Yamaguchi, Miyuki [1 ]
Akiyama, Tomoyo [1 ]
Sasou, Hirohisa [1 ]
Katsumata, Haruka [1 ]
Manabe, Kei [1 ]
机构：
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 13期
关键词：
C-H ACTIVATION; OLIGOARENE-TYPE PHOSPHINES; 4-SUBSTITUTED INDOLES; GRIGNARD-REAGENTS; INTRAMOLECULAR HYDROAMINATION; COMBINATORIAL SYNTHESIS; 2-SUBSTITUTED INDOLES; SONOGASHIRA REACTION; EFFICIENT SYNTHESIS; COUPLING REACTIONS;
D O I：
10.1021/acs.joc.6b00824
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Disubstituted benzo[b]furans were synthesized by ortho-selective Sonogashira coupling of dichlorophenols and terminal alkynes, followed by cyclization and Suzuki-Miyaura coupling in one pot, using a palladium-dihydroxyterphenylphosphine (Cy-DHTP) catalyst. The use of substoichiometric amounts of tetrabutylammonium chloride was effective in accelerating the Suzuki-Miyaura coupling. This protocol was also successfully applied to the one-pot synthesis of disubstituted indoles from dichloroaniline derivatives.
引用
收藏
页码：5450 / 5463
页数：14
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