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Expanding the Scope of Photocatalysis: Atom Transfer Radical Addition of Bromoacetonitrile to Aliphatic Olefins
Author(s) -
Voutyritsa Errika,
Triandafillidi Ierasia,
Kokotos Christoforos G.
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800110
Subject(s) - photocatalysis , chemistry , catalysis , functional group , scope (computer science) , substrate (aquarium) , combinatorial chemistry , photoredox catalysis , organocatalysis , photochemistry , organic chemistry , enantioselective synthesis , polymer , oceanography , computer science , programming language , geology
Abstract An efficient photocatalyzed bromocyanomethylation of alkenes is reported. Among a range of organocatalysts and metal complexes, Ir(ppy) 3 proved to be the best photocatalyst in promoting the addition of BrCH 2 CN to olefins. This photocatalytic atom transfer protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields. In addition, linchpin catalysis was developed, since the bromo group can undergo further transformation into useful functional groups, such as the synthesis of amino acids.