Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation and Heck Cyclization
Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation and Heck Cyclization
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DOI：
10.1021/acs.orglett.5b03390
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发表时间：
2016-01-15
期刊：
影响因子：
5.2
通讯作者：
Ichikawa, Junji
中科院分区：
文献类型：
--
作者：
Fujita, Takeshi;Sugiyama, Kazuki;Ichikawa, Junji
通过钯催化的亲核试剂的1，1-二氟烯丙基化反应和分子内Heck反应合成了含二氟亚甲基的杂环化合物。3-溴-3，3-二氟丙烯的烯丙基取代反应在不重排的情况下被异核试剂区域选择性地完成，得到相应的1，1-二氟烯丙基化合物，其Heck环化反应以5-exo方式进行，得到环二氟吲哚啉和二氢苯并呋喃。它们的脱氟烯丙基取代进一步得到2-氟吲哚和2-氟苯并呋喃。
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.