Iron(II)‐Catalyzed Cyanoalkylsulfonylation/Annulation Cascades toward Functionalized Sulfonylated Pyrrolidone Alkylnitriles. Issue 8 (13th April 2023)

• Record Type: Journal Article
• Authors: Huang, Jiapian; Xu, Shujuan; Zhu, Jia; Chen, Zhiyuan
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 8(2023)
• Page Start: 1179
• Page End: 1184
• Publication Date: 2023-04-13
• Subjects: Fe-catalysis -- cyanoalkylsulfonylation -- pyrrolidone -- cyanoalkyl radical -- sulfone; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202201336
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Under heating conditions, an iron(II)‐catalyzed cascade cyanoalkylsulfonylation/cyclization reaction is developed to produce cyanoalkylsulfonylated pyrrolidones bearing with a free CN moiety. This alkyl radical disconnection and cascade annulation protocol enjoys chemo‐ and regioselectivity with the tolerance toward a range of functional groups. The reactive cyanoalkyl radical, which was originated from the ring‐opening reaction of a cyclic imine radical, was found to be capable of capturing the in‐situ generated "SO2 " species from DABSO, thus leading to the production of a cyanoalkyl sulfonyl radical and the subsequent alkene annulation sequences. Abstract :