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
收藏
页码：248 / 251
页数：4
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