Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides

Abstract

A mild and efficient visible-light-mediated diarylation of N-arylacrylamides with aryl diazonium salts under mild conditions has been developed. This method provides convenient access to a variety of useful 3,3-disubstituted oxindoles by constructing two C-C bonds in one step.

Silver-Catalyzed Tandem Radical Cyclization for the Synthesis of 3,3'-Disubstituted Oxindoles

“…此外, 官能团化的氧化吲哚 也在合成多种杂环化合物的初始原料中有着广泛的应 用 [2] . 尤其是包括 3-(2-氧代丁基)-吲哚-2-酮在内的氧化 吲哚骨架, 因其良好的生物活性而经常用于制药试剂和 天然产物中 [3] .…”

Synthesis of Oxindoles via Iron‐Mediated Hydrometallation‐Cyclization of N‐Arylacrylamides

“…In addition, acylation,,,, sulfonylation,, azidolation, hydroxylalkylation, alkylation, and aryltrifluoromethylthiolation of N ‐arylacrylamides were also reported to deliver various functionalized oxindoles. Even more impressive is that the groups of Zou and Zhu were able to show that photoredox catalysts could be employed to catalyze the reaction of phenyldiazonium salts or alkyl carboxylic acids with N ‐arylacrylamides to give phenyl‐ or alkyl‐substituted oxindoles. Despite all these advances, development of efficient methods for the synthesis of oxindoles remains an attractive goal.…”

Synthesis ofN-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

“…Considering the importance of CF 3 ‐containing oxindoles, Zhu and coworkers subsequently developed a visible‐light‐induced trifluoromethylation of N ‐aryl acrylamides by using Togni's reagent as the “CF 3 ” source . In addition, the similar visible‐light‐promoted cascade radical addition/cyclization pathway to 3,3‐disubstituted 2‐oxindoles has been described by using fluoroalkylsulfonyl chlorides and aryl diazonium salts as the radical precursors.…”