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Graphene‐Oxide‐Catalyzed Cross‐Dehydrogenative Coupling of Oxindoles with Arenes and Thiophenols
Author(s) -
Wu Hongru,
Qiu Chuntian,
Zhang Zhaofei,
Zhang Bing,
Zhang Shaolong,
Xu Yangsen,
Zhou Hongwei,
Su Chenliang,
Loh Kian Ping
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901224
Subject(s) - chemistry , catalysis , functional group , combinatorial chemistry , coupling reaction , oxide , coupling (piping) , reaction conditions , molecule , graphene , quinone , photochemistry , nanotechnology , organic chemistry , mechanical engineering , materials science , engineering , polymer
Abstract Here, we explore the GO‐catalyzed cross‐dehydrogenative coupling of oxindoles with arenes and thiophenols for the rapid synthesis of 3‐aryloxindoles and 3‐sulfenylated oxindoles. Control experiments and small‐molecule mimicking studies reveal that the acidic nature and quinone‐type functionalities of GO are synergistically utilized for the coupling reaction. The reaction proceeds under simple and mild reaction conditions, exhibits good functional group tolerance, and can be easily scaled up to the gram level.