Iodine-mediated aminosulfonylation of alkenyl sulfonamides with sulfonyl hydrazides: synthesis of sulfonylmethyl piperidines, pyrrolidines and pyrazolines

Xu, Zhongqi; Wang, Wenbo; Zheng, Lin-Chuang; Li, Lin; Duan, Lili; Li, Yue‐Ming

doi:10.1039/c9ob01847f

Cited by 10 publications

(12 citation statements)

References 49 publications

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“… [37b] Recently, Li and co‐workers reported an iodine‐mediated aminosulfonylation of alkenyl sulfonamides, and in this reaction, a variety of sulfonylmethyl piperidines, pyrrolidines and pyrazolines could be obtained in moderate to excellent yields (Scheme 7 c). [37c] …”

Section: Iodine‐promoted C−s Bonds Formationmentioning

confidence: 99%

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Zhang

Wang

Jiang

et al. 2020

Chemistry A European J

102

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Sulfur-containing scaffold, as aubiquitous structural motif, has been frequently used in natural products, bioactive chemicals and pharmaceuticals, particularly CÀS/NÀS bonds are indispensable in many biological importantc ompounds and pharmaceuticals. Development of mild and general methods for CÀS/NÀSb onds formation hasg reat significance in modern research. Iodine and its derivativesh ave been recognizeda si nexpensive,e nvironmentally benign and easy-handled catalysts or reagents to promote the construction of CÀS/NÀSb onds under mild reactionc onditions, with good regioselectivities andb road substrate scope.E specially based on this, severaln ew strategies, such as oxidation relay strategy,havebeen greatlydeveloped and accelerated the advancement of this field. This review focuses on recent advances in iodine and its derivatives promoted hybridized CÀS/NÀSbonds formation.The features and mechanisms of corresponding reactions are summarized and the results of some cases are compared with those of previous reports. In addition, the future of this domain is discussed.

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Section: Iodine‐promoted C−s Bonds Formationmentioning

confidence: 99%

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Zhang

Wang

Jiang

et al. 2020

Chemistry A European J

102

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show abstract

“…Subsequently, the same group used a similar strategy to synthesize sulfonylated pyrazolines, which achieved radical tandem cyclization/oxysulfonylation of β,γ‐unsaturated tosyl hydrazones under mild conditions (Scheme 49). [69] …”

Section: Radical Strategies For Cyclization Of βγ‐Unsaturated Hydrazones and Oximesmentioning

confidence: 99%

Radical Cascade Reactions of β,γ‐Unsaturated Hydrazones/Oximes

2021

Adv Synth Catal

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Radical cascade cyclization of β,γ‐unsaturated hydrazones/oximes has recently emerged as an efficient and powerful protocol for the construction of diverse and valuable functionalized pyrazolines and isoxazolines. In this review, three catalytic ways of radical cascade cyclization of β,γ‐unsaturated hydrazones/oximes are summarized and classified; these are transition‐metal‐catalyzed systems, transition‐metal‐free systems, and photo‐/electrocatalytic systems, respectively. Through these methods, various functional groups are installed on the pyrazoline and isoxazoline skeletons to enrich the small organic molecule library.

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“…The aminosulfonylation of alkenyl sulfonamides with sulfonyl hydrazides for the synthesis of sulfonylmethyl piperidines, pyrrolidines and pyrazolines was also realized by this group using iodine as the catalyst and TBHP as the oxidant (Scheme 94). [108] The sulfonylation of vinyl azides for the synthesis of sulfonylated N-unsubstituted enamines via a chain of chemical and electrochemical transformations was disclosed by Terent'ev group. [109] Ammonium iodide can be applied as both a supporting electrolyte and a redox catalyst in this reaction.…”

Section: Sulfonylation/noncyclization With Alkenesmentioning

confidence: 99%

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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Iodine-mediated aminosulfonylation of alkenyl sulfonamides with sulfonyl hydrazides: synthesis of sulfonylmethyl piperidines, pyrrolidines and pyrazolines

Abstract: Using iodine as the catalyst, TBHP as the oxidant, and sulfonyl hydrazides as the sulfonyl radical sources, a variety of sulfonylmethyl piperdines, pyrrolidines and pyrazolines could be obtained in moderate to excellent yields.

Cited by 10 publications

References 49 publications

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Radical Cascade Reactions of β,γ‐Unsaturated Hydrazones/Oximes

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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