Abstract

Reactions of 1,1,1-trifluoro-2-iodoethane with alkylalkenes and silyl enol ethers were performed in the presence of a catalytic amount of fac-Ir(ppy)₃ and an excessive amount of Hünig’s base in acetonitrile irradiated by a 24 W fluorescent lamp under nitrogen atmosphere for 48 hours. The visible-light-induced photoredox reactions introduce simultaneously a 2,2,2-trifluoroethyl group and an iodine atom to both sides of the double bond of ordinary alkenes via an atom-transfer radical addition (ATRA). The same reaction with silyl enol ethers generates β-trifluoromethyl ketones, which are typically a challenge to synthesize. The reactions proved to be tolerant of a variety of functionalities.

Reactions of 1,1,1-trifluoro-2-iodoethane with alkylalkenes and silyl enol ethers were performed in the presence of a catalytic amount of fac-Ir(ppy)₃ and an excessive amount of Hünig’s base in acetonitrile irradiated by a 24 W fluorescent lamp under nitrogen atmosphere for 48 hours. The visible-light-induced photoredox reactions introduce simultaneously a 2,2,2-trifluoroethyl group and an iodine atom to both sides of the double bond of ordinary alkenes via an atom-transfer radical addition (ATRA). The same reaction with silyl enol ethers generates β-trifluoromethyl ketones, which are typically a challenge to synthesize. The reactions proved to be tolerant of a variety of functionalities.

中文翻译：

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可见光诱导的1,1,1-三氟-2-碘乙烷与烷基烯烃和甲硅烷基烯醇醚的光催化反应

摘要

1,1,1-三氟-2-碘乙烷与烷基烯烃和甲硅烷基烯醇醚的反应是在催化量的fac -Ir（ppy）₃和过量的Hünig碱在24 W辐射的乙腈中进行的荧光灯在氮气气氛下放置48小时。可见光诱导的光氧化还原反应通过原子转移自由基加成（ATRA）同时将2,2,2-三氟乙基和碘原子引入普通烯烃的双键的两侧。与甲硅烷基烯醇醚的相同反应产生β-三氟甲基酮，这通常是合成的挑战。该反应被证明可以耐受多种功能。

1,1,1-三氟-2-碘乙烷与烷基烯烃和甲硅烷基烯醇醚的反应是在催化量的fac -Ir（ppy）₃和过量的Hünig碱在24 W辐射的乙腈中进行的荧光灯在氮气气氛下放置48小时。可见光诱导的光氧化还原反应通过原子转移自由基加成（ATRA）同时将2,2,2-三氟乙基和碘原子引入普通烯烃的双键的两侧。与甲硅烷基烯醇醚的相同反应产生β-三氟甲基酮，这通常是合成的挑战。该反应被证明可以耐受多种功能。