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One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
Author(s) -
Reitti Marcus,
Villo Piret,
Olofsson Berit
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603175
Subject(s) - hypervalent molecule , chemistry , regioselectivity , nitration , reagent , aryl , catalysis , iodine , combinatorial chemistry , surface modification , transition metal , ligand (biochemistry) , coupling reaction , organic chemistry , alkyl , biochemistry , receptor
A transition‐metal‐free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one‐pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.