I2‐Promoted Direct C−H Sulfenylation of Isoquinolin‐1(2H)‐ones with Sulfonyl Chlorides. Issue 1 (16th December 2020)

• Record Type: Journal Article
• Authors: Yang, Cai‐Yun; Li, Xia; Liu, Bo; Huang, Guo‐Li
• Is Part Of: European journal of organic chemistry. Issue 1(2021)
• Page Start: 117
• Page End: 124
• Publication Date: 2020-12-16
• Subjects: C−H functionalization -- Iodine -- Isoquinolin-1(2H)-ones -- Sulfenylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202001371
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A simple, efficient, and green method for the iodine‐promoted regioselective C‐4 sulfenylation of isoquinolin‐1(2 H )‐ones using commercially available aryl sulfonyl chlorides as the sulfur source was described under metal‐ and solvent‐free conditions. The reaction proceeded smoothly under simple conditions to obtain 4‐arylthioisoquinolin‐1(2 H )‐ones in moderate to good yields, and showed high regioselectivity, broad substrate scope, and good functional group tolerance. A radical reaction mechanism involving ArS . radicals as key intermediates is proposed for the present transformation. Abstract : Iodine‐promoted regioselective C‐4 sulfenylation of isoquinolin‐1(2 H )‐ones using commercially available aryl sulfonyl chlorides as the sulfur source under metal‐ and solvent‐free conditions was described. These methods provide an alternative and facile synthetic route to access a series of 4‐arylthio‐substituted isoquinolin‐1(2 H )‐one derivatives in moderate to good yields. This is a useful, time‐efficient, and scalable procedure for the construction of C(sp 2 )−S bonds.