Synthesis ( IF 2.2 ) Pub Date : 2018-04-04 , DOI: 10.1055/s-0037-1609447 Koji Hirano 1 , Masahiro Miura 1 , Nobutaka Otomura 1 , Yuto Okugawa 1
|
Published as part of the Special Topic Photoredox Methods and their Strategic Applications in Synthesis
Abstract
An N-bromosuccinimide (NBS)-initiated vic-diphosphination of styrenes with diphosphines proceeds under visible-light-promoted Ir(ppy)3 photoredox catalysis to deliver the corresponding 1,2-diphosphinoethane derivatives in good yields. The NBS is a bromine cation source and generates a bromophosphine, which undergoes a single-electron reduction by the excited iridium species to form phosphinyl radicals of key species in the diphoshination reaction. The newly developed photoredox catalysis demonstrates better reaction efficiency, functional group compatibility, and scalability than the previous photocatalysis using N-fluorobenzenesulfonimide (NFSI) and silylphosphine.
An N-bromosuccinimide (NBS)-initiated vic-diphosphination of styrenes with diphosphines proceeds under visible-light-promoted Ir(ppy)3 photoredox catalysis to deliver the corresponding 1,2-diphosphinoethane derivatives in good yields. The NBS is a bromine cation source and generates a bromophosphine, which undergoes a single-electron reduction by the excited iridium species to form phosphinyl radicals of key species in the diphoshination reaction. The newly developed photoredox catalysis demonstrates better reaction efficiency, functional group compatibility, and scalability than the previous photocatalysis using N-fluorobenzenesulfonimide (NFSI) and silylphosphine.
中文翻译：
在光氧化还原催化下溴阳离子引发苯乙烯与二膦类化合物的苯乙烯二甲基化
作为特别主题的光氧化还原方法及其在合成中的战略应用的一部分发布
抽象的
一个Ñ溴代琥珀酰亚胺（NBS） -引发的VIC苯乙烯的-diphosphination与下可见光促进的Ir（ppy）二膦前进3 photoredox催化递送相应的1,2- diphosphinoethane衍生物以良好的收率。NBS是溴阳离子源，并生成溴膦，该溴膦通过被激发的铱物种进行单电子还原，从而在二膦酰化反应中形成关键物种的次膦酰基基团。与以前使用N-氟苯磺酰亚胺（NFSI）和甲硅烷基膦的光催化相比，新开发的光氧化还原催化具有更好的反应效率，官能团相容性和可扩展性。
一个Ñ溴代琥珀酰亚胺（NBS） -引发的VIC苯乙烯的-diphosphination与下可见光促进的Ir（ppy）二膦前进3 photoredox催化递送相应的1,2- diphosphinoethane衍生物以良好的收率。NBS是溴阳离子源，并生成溴膦，该溴膦通过被激发的铱物种进行单电子还原，从而在二膦酰化反应中形成关键物种的次膦酰基基团。与以前使用N-氟苯磺酰亚胺（NFSI）和甲硅烷基膦的光催化相比，新开发的光氧化还原催化具有更好的反应效率，官能团相容性和可扩展性。
京公网安备 11010802027423号