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Molecules 2018, 23(8), 1838; https://doi.org/10.3390/molecules23081838

Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents

Department of Chemistry and Biochemistry, The University of Tulsa, 800 S. Tucker Dr., Tulsa, OK 74104, USA
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Academic Editor: John C. Walton
Received: 12 July 2018 / Revised: 18 July 2018 / Accepted: 21 July 2018 / Published: 24 July 2018
(This article belongs to the Special Issue Radical Chemistry)
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Abstract

Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes, sulfonamides, and PhI(OAc)2 under practical and mild reaction conditions has been developed. According to mechanistic studies described within, the reaction proceeds through an initial step involving a radical initiator (generated either by visible-light or heat) to activate the reacting substrates. The reaction provides a synthetically useful and operationally simple, relatively mild alternative to the traditional formation of N-sulfonyl imines that utilizes stable, widely available reagents. View Full-Text
Keywords: visible-light; iodine promoted; N-sulfonyl imine; iodobenzene diacetate (PIDA); sulfonamide; hypervalent iodine; aldimine synthesis; iminoiodinane; nitrogen-centered radical visible-light; iodine promoted; N-sulfonyl imine; iodobenzene diacetate (PIDA); sulfonamide; hypervalent iodine; aldimine synthesis; iminoiodinane; nitrogen-centered radical
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hopkins, M.D.; Brandeburg, Z.C.; Hanson, A.J.; Lamar, A.A. Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents. Molecules 2018, 23, 1838.

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