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Reitti M, Villo P, Olofsson B. One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts. Angew Chem Int Ed Engl. 2016;55(31):8928-32doi: 10.1002/anie.201603175.
Reitti, M., Villo, P., & Olofsson, B. (2016). One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts. Angewandte Chemie (International ed. in English), 55(31), 8928-32. https://doi.org/10.1002/anie.201603175
Reitti, Marcus, et al. "One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts." Angewandte Chemie (International ed. in English) vol. 55,31 (2016): 8928-32. doi: https://doi.org/10.1002/anie.201603175
Reitti M, Villo P, Olofsson B. One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts. Angew Chem Int Ed Engl. 2016 Jul 25;55(31):8928-32. doi: 10.1002/anie.201603175. Epub 2016 Jun 08. PMID: 27272891; PMCID: PMC5089574.
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Angew Chem Int Ed Engl. 2016 Jul 25;55(31):8928-32. doi: 10.1002/anie.201603175. Epub 2016 Jun 08.

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

Angewandte Chemie (International ed. in English)

Marcus Reitti, Piret Villo, Berit Olofsson

Affiliations

  1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
  2. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden. [email protected].

PMID: 27272891 PMCID: PMC5089574 DOI: 10.1002/anie.201603175

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.

© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords: arylation; density functional calculations; hypervalent compounds; oxidation; reaction mechanisms

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