Transition-Metal-Free TBAI-Facilitated Addition–Cyclization of N‑Methyl‑N‑arylacrylamides with Arylaldehydes or Benzenesulfonohydrazides: Access to Carbonyl- and Sulfone-Containing N‑Methyloxindoles

A highly efficient addition–cyclization of N-methyl-N-arylacrylamides with arylaldehydes or benzene­sulfono­hydrazides was developed using a catalytic amount of the quaternary ammonium salt (TBAI) under metal-free conditions, leading to the carbonyl- and sulfone-containing oxindoles. Compared to pre...

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Published inJournal of organic chemistry Vol. 81; no. 12; pp. 5181 - 5189
Main Authors Ji, Peng-Yi, Zhang, Ming-Zhong, Xu, Jing-Wen, Liu, Yu-Feng, Guo, Can-Cheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROOM-TEMPERATURE
ACTIVATED ALKENES
3,3-DISUBSTITUTED OXINDOLES
CF3-CONTAINING OXINDOLES
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
C BOND FORMATION
NATURAL-PRODUCTS
LIGHT PHOTOREDOX CATALYSIS
H FUNCTIONALIZATION CASCADE
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Summary:A highly efficient addition–cyclization of N-methyl-N-arylacrylamides with arylaldehydes or benzene­sulfono­hydrazides was developed using a catalytic amount of the quaternary ammonium salt (TBAI) under metal-free conditions, leading to the carbonyl- and sulfone-containing oxindoles. Compared to previous methods, which require excessive amounts of explosive organic peroxides and precious or toxic metal reagents, the present protocol, which gave access to 3,3-disubstituted oxindoles, is a safe and green approach, resulting in the formation of various useful carbonyl- and sulfone-containing oxindoles in yields of 40–94%.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00773