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

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)? 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.

SUBMITTER: Hopkins MD 

PROVIDER: S-EPMC6222766 | biostudies-other | 2018 Jul

REPOSITORIES: biostudies-other

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Visible-Light, Iodine-Promoted Formation of <i>N</i>-Sulfonyl Imines and <i>N</i>-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents.

Hopkins Megan D MD   Brandeburg Zachary C ZC   Hanson Andrew J AJ   Lamar Angus A AA  

Molecules (Basel, Switzerland) 20180724 8

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 <i>N</i>-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  ...[more]