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Three‐Component Azidation of Styrene‐Type Double Bonds: Light‐Switchable Behavior of a Copper Photoredox Catalyst
Author(s) -
Fumagalli Gabriele,
Rabet Pauline T. G.,
Boyd Scott,
Greaney Michael F.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502980
Subject(s) - chemistry , double bond , styrene , regioselectivity , reagent , azide , photochemistry , photoredox catalysis , surface modification , bromide , copper , catalysis , methanol , polymer chemistry , combinatorial chemistry , organic chemistry , photocatalysis , copolymer , polymer
[Cu(dap) 2 ]Cl effectively catalyzes azide addition from the Zhdankin reagent to styrene‐type double bonds, and subsequent addition of a third component to the benzylic position. In the presence of light, a photoredox cycle is implicated with polar components such as methanol or bromide adding to a benzylic cation. In the absence of light, by contrast, double azidation takes place to give diazides. Therefore, regioselective double functionalization can be achieved in good to excellent yields, with a switch between light and dark controlling the degree of azidation.