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One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts.

ABSTRACT: 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.

SUBMITTER: Reitti M

PROVIDER: S-EPMC5089574 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts.

Reitti Marcus M Villo Piret P Olofsson Berit B

Angewandte Chemie (International ed. in English) 20160608 31

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 ...[more]

PMID: 27272891

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