I2-Promoted Direct C-H Sulfenylation of Isoquinolin-1(2H)-ones with Sulfonyl Chlorides

A simple, efficient, and green method for the iodine-promoted regioselective C-4 sulfenylation of isoquinolin-1(2H)-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(2H)-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.

Automated summary

A simple, efficient, and green method for regioselective C-4 sulfenylation of isoquinolin-1(2H)-ones was described using aryl sulfonyl chlorides as the sulfur source under metal- and solvent-free conditions. The reaction showed high regioselectivity, broad substrate scope, and good functional group tolerance, and a radical reaction mechanism involving ArS. radicals as key intermediates was proposed.