Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

Beatriz Dedeiras; Catarina S Caldeira; José C Cunha; Clara S B Gomes; M Manuel B Marques

doi:10.3762/bjoc.20.272

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

Beilstein J Org Chem. 2024 Dec 19:20:3281-3289. doi: 10.3762/bjoc.20.272. eCollection 2024.

Authors

Beatriz Dedeiras¹, Catarina S Caldeira^#¹, José C Cunha^#¹, Clara S B Gomes¹, M Manuel B Marques¹

Affiliation

¹ LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA FCT , 2829-516 Caparica, Portugal.

^# Contributed equally.

Abstract

The reactivity of our recently disclosed hypervalent iodine reagents (HIRs) bearing a benzylamine with in situ-generated sulfenate salts was investigated. Under the studied conditions sulfonamides have been obtained in up to 52% yield. This reaction has been extended to a variety of HIRs and sulfenate salts to explore the different reactivity of these new reagents. A plausible mechanism is proposed, suggesting a possible radical pathway.

Keywords: electrophilic amination; hypervalent iodine reagents; sulfinamide; sulfonamide.

Grants and funding

The authors thank the Fundação para a Ciência e Tecnologia (FCT, project 2022.04623.PTDC, fellowship 2022.11629.BD (J.C.). The authors also thank the support by the Associate Laboratory for Green Chemistry – LAQV which is financed by national funds from FCT/MCTES (UIDB/50006/2020 DOI 10.54499/UIDB/50006/2020, UIDP/50006/2020 DOI 10.54499/UIDP/50006/2020, and LA/P/0008/2020 DOI 10.54499/LA/P/0008/2020). FCT/MCTES is also acknowledged for supporting the National NMR Facility (ROTEIRO/0031/2013 − PINFRA/22161/2016, cofinanced by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC), and RECI/BBB-BEP/0124/2012 (X-ray Infrastructure), which was coﬁnanced by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER - 007265).