PEG-Supported Hypervalent Iodine Reagent for Sulfonamide Synthesis

João Macara; Diogo L. Poeira; Jaime A. S. Coelho; M. Manuel B. Marques

doi:10.1055/s-0040-1719828

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(17): 1730-1734
DOI: 10.1055/s-0040-1719828

letter

PEG-Supported Hypervalent Iodine Reagent for Sulfonamide Synthesis

João Macara

^aLAQV@REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, Caparica 2829-516, Portugal

,

Diogo L. Poeira

^aLAQV@REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, Caparica 2829-516, Portugal

,

Jaime A. S. Coelho

^bCentro de Química Estrutural, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal

,

M. Manuel B. Marques ∗

^aLAQV@REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, Caparica 2829-516, Portugal

› Institutsangaben

Abstract

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Abstract

A reusable and recoverable PEG-supported hypervalent iodine reagent is reported. This hypervalent iodine reagent, immobilized in a soluble polymer support, was easily prepared in six steps from PEG-OH 2000. This reagent was successfully applied in a mild sulfonamide synthesis using a sulfinate salt and an amine in up to 95% yield. The use of the soluble polymer allowed a facile workup procedure and reaction monitoring, by simple precipitation and filtration of the reagent, with an easy recovery and subsequent re-oxidation and reuse. This approach greatly improves the sustainability of this sulfonamide synthesis method, avoiding frequent preparation of reagents and generation of waste during the purification steps.

Key words

PEG - hypervalent iodine - sulfonamide synthesis - sustainable synthesis - soluble polymer support

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