Light‐Induced Dealkylation of Benzamides in Aqueous Solution

Abstract

Supporting information for this article is given via a link at the end of the document.

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

“…The reactions of N-ethyl-N-isopropylbenzamide (3), N,Ndiethylbenzamide (4), N-isopropyl-N-benzylbenzamide (5), Nmethyl-N-isopropylbenzamide (6), and N-isopropyl-Nphenylbenzamide (7) As shown in Scheme 3A, the parallel kinetic isotope experiments of 1a and 1a-D gave a KIE value of 1.23, indicating that the cleavage of aryl C−H bond is not the rate-limiting step. Based on this data and previous reports 16 , a plausible reaction mechanism for 1a is proposed in Scheme 3B. Upon heating, sulfate radical anion is generated from persulfate and then undergoes hydrogen atom transfer (HAT) with 1a to form alkyl radical intermediate I.…”