RuII‐Catalyzed ortho‐Sulfonamidation of α‐Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C−H Activation. Issue 12 (18th October 2017)

• Record Type: Journal Article
• Authors: Krishna Rao, Medikonda V.; Reddy, Keesari Nagarjuna; Sridhar, Balasubramaniam; Subba Reddy, Basi V.
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 12(2017)
• Page Start: 1851
• Page End: 1856
• Publication Date: 2017-10-18
• Subjects: arenes -- C−H activation -- regioselectivity -- ruthenium -- sulfonamidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700356
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A method has been developed for the sulfonamidation of tetralones and 1, 4‐naphthoquinones by using sulfonyl azides in the presence of a Ru II /Ag I catalytic system. In case of tetralones, C−H bond functionalization occurred exclusively at the ortho position, whereas 1, 4‐addition was the main transformation for 1, 4‐naphthoquinones. This method is highly regioselective and was successfully utilized for the synthesis of sivelestat, an inhibitor of human neutrophil elastase. Abstract : Amide other reactions : A method has been developed for the sulfonamidation of α‐tetralones and 1, 4‐naphthoquinones by using sulfonyl azides and a Ru II /Ag I catalytic system (see scheme; DCE=1, 2‐dichloroethane). Tetralones underwent C−H bond functionalization exclusively at the ortho position, whereas 1, 4‐addition was the primary reaction for 1, 4‐naphthoquinone. This highly regioselective approach was also used to synthesize sivelestat, an inhibitor of human neutrophil elastase.