SYNTHESIS OF ISOCHROMANES AND ISOTHIOCHROMANES BEARING FLUORINATED ONE-CARBON UNITS VIA INTRAMOLECULAR CYCLIZATIONS OF ORTHO-SUBSTITUTED α-(TRIFLUOROMETHYL)STYRENES

被引：9

作者：

Ichikawa, Junji ^{[1
]}

Ikeda, Masahiro ^{[1
]}

Hattori, Masahiro ^{[1
]}

机构：

[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Dept Chem, Tsukuba, Ibaraki 3058571, Japan

来源：

HETEROCYCLES | 2009年 / 77卷 / 02期

关键词：

Trifluoromethyl Group; Difluoromethylene Group; Addition; Substitution; BUILDING-BLOCK; AQUEOUS-MEDIA; TRIFLUOROMETHYL; HETEROCYCLES; ACID;

D O I：

10.3987/COM-08-S(F)114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-(Trifluoromethyl)styrenes bearing a nucleophilic oxygen or sulfur atom tethered by a methylene or methyne unit at the ortho carbon were prepared by the coupling reaction of 2-bromo-3,3,3-trifluoropropene with aryl iodides via (3,3,3-trifluoroprop-1-en-2-yl) boronic acid. The styrenes thus obtained readily undergo an intramolecular nucleophilic addition or substitution (S(N)2'-type) of the oxygen and sulfur under basic conditions, leading to 4-trifluoromethyl- or 4-difluoromethylene-substituted isochromanes and isothiochromanes, respectively.

引用

页码：1285 / 1296

页数：12

共 13 条

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