Citation: Song Mengmeng, Zhang Zhiguo, Zheng Dan, Li Xiang, Liang Rui, Zhao Xu'na, Shi Lei, Zhang Guisheng. Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2433-2441. doi: 10.6023/cjoc202001007 shu

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

Song Mengmeng ^a ,
Zhang Zhiguo ^a,, ,
Zheng Dan ^b ,
Li Xiang ^a ,
Liang Rui ^a ,
Zhao Xu'na ^a ,
Shi Lei ^a ,
Zhang Guisheng ^a,,

a.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
b.
Quality and Technique Supervision, Inspection and Testing Center of Xuchang City, Xuchang, Henan 461000

Corresponding author: Zhang Zhiguo, Zhangzg@htu.edu Zhang Guisheng, zgs6668@yahoo.com
Received Date: 4 January 2020
Revised Date: 16 May 2020
Available Online: 25 May 2020
Fund Project: Program for Changjiang Scholars and Innovative Research Team in University IRT1061the Key Project of Henan Educational Committee 18A150009Industrial Process Intelligent Control Innovation and Talent Recruitment Base D17007National Natural Science Foundation of China 21702051Project supported by the National Natural Science Foundation of China (Nos. U1604285, 21772032, 21702051), Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1061), Industrial Process Intelligent Control Innovation and Talent Recruitment Base (No. D17007) and the Key Project of Henan Educational Committee (No. 18A150009)National Natural Science Foundation of China 21772032National Natural Science Foundation of China U1604285

Figures(1)

An efficient Dess-Martin periodinane (DMP)-promoted dearylation of N-arylsulfonamides was developed through a highly selective oxidative cleavage of the inert C(aryl)-N bonds in secondary sulfonamides while leaving the S-N bond unchanged. This metal-free reaction proceeds under mild conditions and provides access to various biologically important primary sulfonamides, some of which are otherwise unattainable using conventional aminolysis and hydrolysis methods. The concise and efficient dearylation reaction provides the use of an aryl group as a removable protecting sulfonamide group under metal catalyst-free conditions.
- Dess-Martin periodinane (DMP),
- C(aryl)-N bond cleavage,
- oxidation,
- metal-free reaction,
- sulfonamide
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