Iodine-catalyzed cascade annulation of alkynes with sodium arylsulfinates: assembly of 3-sulfenylcoumarin and 3-sulfenylquinolinone derivatives

Wu, Wanqing; An, Yanni; Li, Jianxiao; Yang, Shaorong; Zhu, Zhongzhi; Jiang, Huanfeng

doi:10.1039/c7qo00326a

Cited by 52 publications

(20 citation statements)

References 83 publications

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“…Recently, Jiang and co‐workers developed a versatile protocol to 3‐sulfenylcourmain and 3‐sulfenylquinolinone derivatives through iodine‐promoted cascade cyclization/sulfenylation of alkynes with sodium arylsulfinates (Scheme 3 a). [26a] Preliminary mechanistic studies indicated DMSO was essential in the reaction to recycle iodine. Meanwhile, disulfide was also applicable under standard conditions, which suggested that it might be the intermediate in this reaction.…”

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

111

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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

111

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“…In 2017, Wu and co‐workers [242] reported iodine/P(Cy) 3 mediated electrophilic cyclization to afford 3‐sulfenylcoumarin or 3‐sulfenylquinolinones ( 385 , 386 ). The methodology was successfully applied by treating alkynoates or alkynamides scaffolds ( 86 , 384 ) with sodium sulfinates ( 49 ) in ionic liquid 1‐carboxymethyl‐3‐methylimidazolium tetrafluoroborate ([C 2 O 2 mim]BF 4 ).…”

Section: Sulfenylationmentioning

confidence: 99%

“…Finally, it was proposed that nucleophilic attack of enaminones on electrophile (RSI) (26 A) (generated in situ from heterocyclic thiones) resulted into sulfenylated enaminones (Scheme 127). [241] In 2017, Wu and co-workers [242] reported iodine/P(Cy differently substituted sodium aryl sulfinates were investigated. The reaction tolerated well sodium aryl sulfinates substituted with both electron donating and withdrawing substituents, and resulted into superior yields in case of electron donating groups.…”

Section: Iodine Mediated Sulfenylationmentioning

confidence: 99%

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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Transition metal‐free sulfenylation of C−H bonds for C−S bond formation has recently emerged as sustainable protocols for the functionalisation of various molecules. Researchers have extensively developed such protocols for the construction of biologically relevant sulfur scaffolds. There has been a gradual shift from metal‐catalyzed to metal‐free C−S bond formation methodologies, because the latter offer environmentally benign and inherently safe access to novel synthetic routes in organic chemistry. The present review offers a dynamic discussion on recent advances in transition metal‐free C−S bond formation via C−H bond functionalization using different surrogate sulfenylating reagents. The review has comprehensively been devoted to radical and ionic mechanistic approaches. Some simple and eco‐friendly reagents for sulfenylation viz. tertbutyl hydrogen peroxide (TBHP), hydrogen peroxide (H2O2), iodine/potassium persulphate (I2/K2S2O8), inorganic bases, strong organic acids, iodine, I2/triphenyl phosphine (PPh3), N‐chlorosuccinamide (NCS), N‐bromosuccinamide (NBS), potassium iodate (KIO3), I2/bovine serum albumin (BSA), tetrabutyl ammonium iodide (TBAI)/HBr and graphene oxide along with their mechanistic approach has been detailed in this review. Moreover, modern methods for the C−S bond formation i. e., biocatalyst, electrochemical and visible light induced sulfenylation, and traditional sulfenylation methodologies have also been incorporated.

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“…Wu, Jiang and co-workers 211 , ICl and TBAI were considered in a variety of solvents. After extensive screening, the optimal conditions were identified and used to explore the generality and scope of this reaction.…”

Section: Synthesis Of Oxygen-containing Heterocyclesmentioning

confidence: 99%

New frontiers in the transition-metal-free synthesis of heterocycles from alkynoates: an overview and current status

2020

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Iodine-catalyzed cascade annulation of alkynes with sodium arylsulfinates: assembly of 3-sulfenylcoumarin and 3-sulfenylquinolinone derivatives

Abstract: An efficient and environmentally benign iodine-catalyzed cascade cyclization has been achieved to afford functionalized 3-sulfenylcoumarin and 3-sulfenylquinolinone derivatives.

Cited by 52 publications

References 83 publications

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

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

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

New frontiers in the transition-metal-free synthesis of heterocycles from alkynoates: an overview and current status

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