Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation and Heck Cyclization

被引：37

作者：

Fujita, Takeshi ^{[1
]}

Sugiyama, Kazuki ^{[1
]}

Sanada, Shohei ^{[1
]}

Ichitsuka, Tomohiro ^{[1
]}

Ichikawa, Junji ^{[1
]}

机构：

[1] Univ Tsukuba, Fac Pure & Appl Sci, Div Chem, Tsukuba, Ibaraki 3058571, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 02期

关键词：

NUCLEOPHILIC-SUBSTITUTION; ALLYLIC DIFLUORIDES; BOND; HETEROCYCLES; ACTIVATION; ALCOHOLS; ACCESS;

D O I：

10.1021/acs.orglett.5b03390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of difluoromethylene-containing heterocycles was achieved via the palladium-catalyzed 1,1-difluoroallylation of heteronucleophiles followed by intramolecular Heck reaction. The allylic substitution of 3-bromo-3,3-difluoropropene was regioselectively accomplished by heteronucleophiles without rearrangement to give the corresponding 1,1-difluoroallylated compounds whose Heck cyclization proceeded in a 5-exo manner to afford ring-difluorinated indolines and dihydrobenzofurans. Their defluorinative allylic substitution further provided 2-fluoroindoles and 2-fluorobenzofurans.

引用

页码：248 / 251

页数：4

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