Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis of N‐Allylsulfenamides via [2, 3]‐Sigmatropic Rearrangement. Issue 41 (20th October 2020)

• Record Type: Journal Article
• Authors: Makitalo, Cody L.; Yoshimura, Akira; Rohde, Gregory T.; Mironova, Irina A.; Yusubova, Rosa Y.; Yusubov, Mekhman S.; Zhdankin, Viktor V.; Saito, Akio
• Is Part Of: European journal of organic chemistry. Issue 41(2020)
• Page Start: 6433
• Page End: 6439
• Publication Date: 2020-10-20
• Subjects: Hypervalent compounds -- Iodine -- Sigmatropic rearrangement -- Sulfilimines -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000961
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A facile metal‐free [2, 3]‐sigmatropic rearrangement reaction of allyl sulfides via N ‐sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino‐λ 3 ‐iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N ‐allylsulfenamide compounds in moderate to good yields. Several N ‐allylsulfenamide structures have been confirmed by single‐crystal X‐ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino‐λ 3 ‐iodane and the sulfur atom, resulting in the formation of N ‐sulfilimine species, followed by [2, 3]‐sigmatropic rearrangement to form the N ‐allylsulfenamide. Abstract : Imino‐λ 3 ‐iodane and catalytic I2 ‐mediated facile metal‐free [2, 3]‐sigmatropic rearrangement reaction of allyl sulfides producing N ‐allysulfenamiides has been developed