Vicinal Difluoroalkylation and Aminosulfonylation of Alkynes under Photoinduced Conditions

Xiang, Yuanchao; Li, Yuewen; Kuang, Yunyan; Wu, Jie

doi:10.1002/chem.201605336

Cited by 85 publications

(29 citation statements)

References 112 publications

(24 reference statements)

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“…[90b] On the other hand, Rastogia nd colleagues have proposed an intramolecular photocatalyzed difluoromethylation-cyclization of 1,3-diarylpropynones towards the synthesis of difluoromethylated indenones. [90c] Wu and collaborators [91] introduced in 2017 ap hotocatalytic difluoromethylation four-component multistep reaction with excellent atom economy.The reaction involves avicinal difluoroalkylation and aminosulfonylationo fa lkynes. The tandem radicalprocess is depicted in Scheme 34.…”

Section: Difluoromethylation Of Càct Riple Bondsmentioning

confidence: 99%

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Difluoromethylation Reactions of Organic Compounds

Yerien

Barata‐Vallejo

Postigo

2017

Chemistry A European J

394

153

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The relevance of the -CF H moiety has attracted considerable attention from organic synthetic and medicinal chemistry communities, because this group can act as a more lipophilic isostere of the carbinol, thiol, hydroxamic acid, or amide groups. Being weakly acidic, the CF H moiety can establish hydrogen-bonding interactions to improve the binding selectivity of biologically active compounds. Therefore, the hydroxyl, amino, and thio substituents of lead structures are routinely replaced by a CF H motif in drug discovery, with great benefits in the pharmacological activity of drugs and drug candidates and agrochemicals. Consequently, the late-stage introduction of CF H is a sought-after strategy in designing bioactive compounds. Secondly, but nonetheless relevant and meaningful, is the study of synthetic pathways to introduce a CF -Y moiety (Y≠H, F) into organic substrates because compounds that contain a CF -Y functionality have also found vast applications in medicinal chemistry and in other areas, such as that of fungicides, insecticides, etc., and thus, this functionality deserves special attention. Although emphasis is made on difluoromethylation strategies to functionalize different families of organic compounds, three main methodological protocols will be presented in this review article for the late-stage introduction of a CF H or CF Y moieties into organic substrates: i) a metal-photoredox catalysis; ii) through transition metal-catalyzed thermal protocols; and iii) from transition-metal-free strategies.

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Section: Difluoromethylation Of Càct Riple Bondsmentioning

confidence: 99%

“…The authors [91] studied the mechanism of this multicomponent reactiono fa lkynes, and DABCO(SO 2 ) 2 with hydrazines, adding TEMPO. As expected,t he reactioni st erminated in the presenceo f2 .0 equiv of TEMPO.…”

Section: Difluoromethylation Of Càct Riple Bondsmentioning

confidence: 99%

Difluoromethylation Reactions of Organic Compounds

Yerien

Barata‐Vallejo

Postigo

2017

Chemistry A European J

394

153

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“…Further exploration revealed that alkyl–X bond could be dissociated under visible light irradiation in the presence of photoredox catalyst. The photoinduced vicinal difluoroalkylation and aminosulfonylation of alkynes under photocatalysis could be accomplished through a multicomponent reaction of ethyl 2‐bromo‐2,2‐difluoroacetate, alkynes, DABCO · (SO 2 ) 2 , and hydrazines catalyzed by 9‐mes‐10‐methyl acridinium perchlorate in the presence of visible light (Scheme ) . This four‐component reaction was highly effective, affording ( E )‐ethyl 2,2‐difluoro‐4‐aryl‐4‐sulfamoylbut‐3‐enoates in good yields with excellent chemoselectivity and stereoselectivity.…”

Section: Photo‐initiated Formation Of Radical With the Subsequent mentioning

confidence: 99%

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Xie

et al. 2019

Eur J Org Chem

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Recent advances in the photoinduced sulfonylation reactions through the insertion of sulfur dioxide are summarized. Among the approaches developed in the sulfonylation reactions, the insertion of sulfur dioxide via radical process can be accomplished with the assistance of photoredox catalysis in the presence of visible light or under ultraviolet irradiation, depending the substrates used in the reactions. Under ultraviolet irradiation, the conversion can be completed under metal‐ and additive‐free conditions. It is noteworthy that alkyl halides possessing eliminable β‐hydrogen atom are effective as alkyl radical precursors with the insertion of sulfur dioxide. Two parts, according to the photoinduced reaction pathways, are introduced: (a) photo‐initiated formation of radical with the subsequent capture of sulfur dioxide; (b) photo‐assisted single electron transfer (SET) after insertion of sulfur dioxide. During the transformation, an oxidative or reductive single electron transfer would occur under visible light photoredox catalysis.

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“…[13] With the development of organic synthesis, rapid progress has been witnessed with the fixation of sulfur dioxide by using inorganic sulfites or the sulfur dioxide surrogate of 1,4diazabicyclo[2.2.2]octane-sulfur dioxide [DABSO: DABCO-bis(sulfur dioxide)] as the source. [14,15] These methods provide efficient protocols for various synthetically difficult pharmaceutical targets. [16] As useful sulfonylation reagents, sodium sulfinates are widely applied to build various functional sulfonyl-containing compounds, such as sulfonamides and sulfones.…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

et al. 2020

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A transition‐metal‐free approach to benzyl sulfones by using sodium sulfinates and benzyl ammonium salts is described. The protocol provides a simple and direct method to realize the C−N bond cleavage in the presence of readily available Cs2CO3. During the reaction process, a range of functional groups with respect to both sodium sulfinates and benzylic ammonium salts were well compatible, leading to various benzyl sulfones in moderate to good yields.

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Vicinal Difluoroalkylation and Aminosulfonylation of Alkynes under Photoinduced Conditions

Cited by 85 publications

References 112 publications

Difluoromethylation Reactions of Organic Compounds

Difluoromethylation Reactions of Organic Compounds

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

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