Nickel-Catalyzed Enantioselective Dearomative Heck-Reductive Allylic Defluorination Reaction of Indoles.
Nickel-Catalyzed Enantioselective Dearomative Heck-Reductive Allylic Defluorination Reaction of Indoles.
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DOI：
10.1021/acs.orglett.3c02092
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发表时间：
2023-08
期刊：
影响因子：
5.2
通讯作者：
Yuanchun Hu;Xiao-Qiu Xu;Weixia Deng;Ren-Xiao Liang;Yi‐Xia Jia
中科院分区：
文献类型：
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作者：
Yuanchun Hu;Xiao-Qiu Xu;Weixia Deng;Ren-Xiao Liang;Yi‐Xia Jia
在此，我们描述了一种镍催化的吲哚与α-三氟甲基烯烃的不对称脱芳芳基-二氟烯丙基化反应。该反应通过一个级联序列进行，包括脱芳Heck环化和还原烯丙基脱芳。以中等至良好的产率（36-77%产率）和优异的对映选择性（高达99%ee）获得了一系列偕-二氟烯丙基取代的吲哚啉。该反应具有广泛的官能团耐受性，放大合成和后期多样化。
Herein, we describe a nickel-catalyzed asymmetric dearomative aryl-difluoroallylation reaction of indoles with α-trifluoromethyl alkenes as an electrophilic coupling partner. The reaction proceeds via a cascade sequence involving dearomative Heck cyclization and reductive allylic defluorination. A series of gem-difluoroallyl substituted indolines are obtained in moderate to good yields (36-77% yield) with excellent enantioselectivity (up to 99% ee). The reaction features broad functional group tolerance, scaled-up synthesis, and late-stage diversification.