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Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2024-04-30 , DOI: 10.1039/d4qo00559g
Weidi Zeng 1 , Mingqiang Li 1 , Shaofeng Wu 1 , Ablimit Abdukade 1 , Lei Zhou 1, 2
Affiliation  

We herein report a base-controlled α- or γ-difluoroallylation of alkylidene malonates with trifluoromethyl alkenes, providing various gem-difluoro-1,5-dienes with excellent regioselectivity. Upon irradiation with visible light in the presence of fac-Ir(ppy)3, the intramolecular crossed [2 + 2] photocycloaddition of gem-difluoro-1,5-dienes leads to the formation of highly substituted bicyclo[2.1.1]hexanes in good to excellent yields via an energy transfer pathway.

中文翻译:

亚烷基丙二酸酯与三氟甲基烯烃的区域选择性二氟烯丙基化:偕二氟-1,5-二烯的合成及其[2 + 2]光环加成

我们在此报告了亚烷基丙二酸酯与三氟甲基烯烃的碱基控制的α-或γ-二氟烯丙基化,提供了具有优异区域选择性的各种二氟-1,5-二烯。在fac -Ir(ppy) 3存在下用可见光照射时,偕-二氟-1,5-二烯的分子内交叉[2 + 2]光环加成导致形成高度取代的双环[2.1.1]己烷通过能量转移途径获得良好至优异的产量。
更新日期:2024-04-30
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