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

页码：5450 / 5463

页数：14

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