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Visible Light Driven Hydro‐/Deuterodefunctionalization of Anilines
Author(s) -
Majek Michal,
Filace Fabiana,
Jacobi von Wangelin Axel
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406461
Subject(s) - chemistry , visible spectrum , hydrogen atom abstraction , photochemistry , radical , combinatorial chemistry , organic chemistry , materials science , optoelectronics
The defunctionalization of anilines is an important strategy in aromatic‐substitution chemistry. Herein, we report on visible light mediated hydro‐ and deuterodediazonations in solutions of DMF. The mild reaction conditions (DMF, RT, no additives) tolerate various functional groups and allow the site‐specific introduction of D atoms to the arene. Mechanistic investigations indicate the participation of photoredox and radical chain pathways and competing abstraction of methyl and formyl hydrogen atoms from DMF.