- Disulfides as Sulfonylating Precursors for the Synthesis of Sulfone-Containing Oxindoles
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The first facile one-pot synthesis of sulfone-containing oxindoles with easily accessible disulfides as the sulfonylating precursors is described. This reaction occurs smoothly under transition metal-free conditions and shows excellent functional group tolerance, allowing the facile and efficient green synthesis of various sulfone-containing oxindoles in aqueous solution. Preliminary mechanistic studies reveal that both water (H2O) and potassium persulfate (K2S2O8) can be the oxygen source of the sulfone groups in the products. (Figure presented.).
- Zhang, Ming-Zhong,Ji, Peng-Yi,Liu, Yu-Feng,Xu, Jing-Wen,Guo, Can-Cheng
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supporting information
p. 2976 - 2983
(2016/09/16)
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- Transition-Metal-Free TBAI-Facilitated Addition-Cyclization of N-Methyl-N-arylacrylamides with Arylaldehydes or Benzenesulfonohydrazides: Access to Carbonyl- and Sulfone-Containing N-Methyloxindoles
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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%.
- Ji, Peng-Yi,Zhang, Ming-Zhong,Xu, Jing-Wen,Liu, Yu-Feng,Guo, Can-Cheng
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p. 5181 - 5189
(2016/07/06)
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- Iron-catalyzed aerobic difunctionalization of alkenes: A highly efficient approach to construct oxindoles by C-S and C-C bond formation
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A novel iron-catalyzed efficient approach to construct sulfone-containing oxindoles, which play important roles in the structural library design and drug discovery, has been developed. The use of readily available benzenesulfinic acids, an inexpensive iron salt as the catalyst, and air as the oxidant makes this sulfur incorporation protocol very efficient and practical. This journal is the Partner Organisations 2014.
- Shen, Tao,Yuan, Yizhi,Song, Song,Jiao, Ning
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p. 4115 - 4118
(2014/04/03)
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- Catalyst-free direct arylsulfonylation of N-arylacrylamides with sulfinic acids: A convenient and efficient route to sulfonated oxindoles
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A simple, efficient and catalyst-free procedure has been developed for the construction of sulfonated oxindoles via the direct arylsulfonylation of N-arylacrylamides with sulfinic acids. The present protocol, which simply utilizes cheap oxidants, readily-available starting materials, and catalyst-free conditions, provides an alternative and highly attractive approach to a series of sulfonated oxindoles with high atom efficiency and excellent functional group tolerance. This journal is the Partner Organisations 2014.
- Wei, Wei,Wen, Jiangwei,Yang, Daoshan,Du, Juan,You, Jinmao,Wang, Hua
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p. 2988 - 2991
(2014/06/10)
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