Direct C(sp3)−H Sulfonylation and Sulfuration Reactions of Isoquinoline‐1, 3(2H, 4H)‐diones under Metal‐free Conditions. Issue 2 (23rd December 2020)

• Record Type: Journal Article
• Authors: Wang, Xing‐Lan; Bai, Xue; Wu, Chun‐Feng; Dong, Yong‐Xi; Zhang, Min; Fan, Ling‐Ling; Tang, Lei; Yang, Yuan‐Yong; Zhang, Ji‐Quan
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 2(2021)
• Page Start: 386
• Page End: 391
• Publication Date: 2020-12-23
• Subjects: Sulfonylation -- sulfuration -- isoquinoline-1, 3-(2H, 4H)-dione -- metal-free conditions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000668
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The first direct C(sp 3 )−H bond sulfonylation and sulfuration reactions of isoquinoline‐1, 3‐(2 H, 4 H )‐diones have been developed under transition‐metal‐free conditions. Using air as the sole oxidant, the C‐4 sulfonylated products of isoquinolones were synthesized using sulfinates as the sulfonating agents and NaI as an iodine source in AcOH/DMSO. The sulfuration reaction was realized for the first time using disulfides as sulfurating partners in a t ‐BuOK/DMF catalytic system. Both procedures undergo a free radical reaction process with the advantages of high atom economy, green reaction conditions, readily accessible materials and broad substrate scope. Abstract : Direct C(sp 3 )‐H bond sulfonylation and sulfuration reactions of isoquinoline‐1, 3‐(2 H, 4 H )‐diones have been developed under transition‐metal‐free conditions. Both procedures undergo a free radical reaction process and air is used as the sole oxidant.