Generation of (E)-β-sulfonyl enamines from sulfur dioxide via a radical process. Issue 8 (23rd February 2021)

• Record Type: Journal Article
• Authors: Tu, Xiaodong; Huang, Jiapian; Xie, Wenlin; Zhu, Tonghao; Wu, Jie
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 8(2021)
• Page Start: 1789
• Page End: 1794
• Publication Date: 2021-02-23
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo01551b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An iron(ii )-catalyzed three-component reaction of O -acyl oximes, sulfur dioxide, and N -vinylacetamides is accomplished. Diverse ( E )-β-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity. Abstract : An iron(ii )-catalyzed three-component reaction of O -acyl oximes, sulfur dioxide, and N -vinylacetamides is accomplished. Diverse ( E )-β-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity under mild conditions. Various sensitive functional groups are compatible, and a broad reaction scope is presented. A plausible mechanism is proposed, which undergoes a radical pathway through a α-carbon radical intermediate generated from iron-catalyzed ring-opening C–C bond cleavage of O -acyl oxime.