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Visible‐Light‐Accelerated Copper(II)‐Catalyzed Regio‐ and Chemoselective Oxo‐Azidation of Vinyl Arenes
Author(s) -
Hossain Asik,
Vidyasagar Adiyala,
Eichinger Christian,
Lankes Christian,
Phan Jenny,
Rehbein Julia,
Reiser Oliver
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201801678
Subject(s) - homolysis , chemistry , radical , catalysis , azide , copper , photochemistry , photocatalysis , ligand (biochemistry) , visible spectrum , iridium , ruthenium , stoichiometry , polymer chemistry , organic chemistry , materials science , biochemistry , receptor , optoelectronics
The visible‐light‐accelerated oxo‐azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap) 2 ]Cl or [Cu(dap)Cl 2 ] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. Cu II is proposed as the catalytically active species, which upon coordinating azide will undergo light‐accelerated homolysis to form Cu I and azide radicals. This activation principle (Cu II ‐X→Cu I +X . ) opens up new avenues for copper‐based photocatalysis.