可見光促進下氟烷基砜對芳基烯烴的自由基氟烷基化反應
發(fā)布時間:2018-10-05 09:26
【摘要】:自由基氟烷基化是向有機分子中引入氟烷基的一類非常重要的方法,也是目前有機化學研究的熱點之一.近幾年來,由于廣泛的官能團兼容性和溫和的反應條件等優(yōu)點,可見光促進的氧化還原催化反應得到了長足的發(fā)展,已經(jīng)成為化學鍵的構(gòu)建和活化的有力工具.因此,光氧化還原催化的自由基氟烷基化反應,作為向有機化合物中引入氟烷基的有效途徑,受到了廣泛關(guān)注.本文報道了我們發(fā)展的氟烷基砜作為一類方便易得的新型氟烷基自由基前體,在可見光氧化還原催化下實現(xiàn)對烯烴的自由基氟烷基化反應.該反應可以高效地向芳基烯烴中引入三氟甲基、二氟甲基、1,1-二氟乙基、苯基二氟甲基等各種含氟烷基基團,并實現(xiàn)對芳基烯烴的雙官能團化轉(zhuǎn)化.
[Abstract]:Free radical fluoroalkylation is a very important method to introduce fluoroalkyl to organic molecules, and it is also one of the hot spots in organic chemistry. In recent years, due to the advantages of extensive functional group compatibility and mild reaction conditions, visible light-induced redox catalytic reactions have been greatly developed and have become a powerful tool for the construction and activation of chemical bonds. Therefore, photoredox catalyzed free radical fluoroalkylation as an effective way to introduce fluoroalkyl into organic compounds has attracted wide attention. The fluoroalkyl sulfone developed by us as a kind of new fluoroalkyl radical precursor which is easy to obtain is reported in this paper. The alkylation of olefins with fluoroalkylation is realized under the catalysis of visible light redox. This reaction can efficiently introduce trifluoromethyl, difluoromethyl 1-difluoroethyl and phenyl difluoromethyl groups into aryl olefins, and realize the difunctional conversion of aryl olefin.
【作者單位】: 中國科學院上海有機化學研究所有機氟化學重點實驗室;Syngenta Jealott’s
【基金】:973計劃(2015CB931900) 國家自然科學基金(21372246,21421002,21472221) 上海市學術(shù)帶頭人計劃(15XD1504400) 中國科學院青年創(chuàng)新促進會(2014231) Syngenta博士生獎學金資助~~
【分類號】:O621.25
[Abstract]:Free radical fluoroalkylation is a very important method to introduce fluoroalkyl to organic molecules, and it is also one of the hot spots in organic chemistry. In recent years, due to the advantages of extensive functional group compatibility and mild reaction conditions, visible light-induced redox catalytic reactions have been greatly developed and have become a powerful tool for the construction and activation of chemical bonds. Therefore, photoredox catalyzed free radical fluoroalkylation as an effective way to introduce fluoroalkyl into organic compounds has attracted wide attention. The fluoroalkyl sulfone developed by us as a kind of new fluoroalkyl radical precursor which is easy to obtain is reported in this paper. The alkylation of olefins with fluoroalkylation is realized under the catalysis of visible light redox. This reaction can efficiently introduce trifluoromethyl, difluoromethyl 1-difluoroethyl and phenyl difluoromethyl groups into aryl olefins, and realize the difunctional conversion of aryl olefin.
【作者單位】: 中國科學院上海有機化學研究所有機氟化學重點實驗室;Syngenta Jealott’s
【基金】:973計劃(2015CB931900) 國家自然科學基金(21372246,21421002,21472221) 上海市學術(shù)帶頭人計劃(15XD1504400) 中國科學院青年創(chuàng)新促進會(2014231) Syngenta博士生獎學金資助~~
【分類號】:O621.25
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1 洪關(guān)林;;酰胺的N—烷基化反應[J];火炸藥;1982年02期
2 牛蓉,盧建軍,李凡,朱素渝,謝克昌;煤的烷基化反應研究進展[J];煤炭轉(zhuǎn)化;2000年02期
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