Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position

Tayu, Masanori; Higuchi, Kazuhiro; Inaba, Masato; Kawasaki, Tomomi

doi:10.1039/c2ob26944a

Cited by 29 publications

(11 citation statements)

References 63 publications

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“…A wide range of nucleophiles competently add to the activated intermediate 268 , including diphenyl sulfoxide (Scheme 45b). 151 Intermediate 270 , formed upon the second sulfoxide addition, can easily undergo Kornblum-type oxidation to form the corresponding benzylic ketone 271 .…”

Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…In addition to methanol, other carbon- and heteroatom-nucleophiles 132 were also directly introduced into 131 to form 133 in excellent yields. 33` b c Similarly, a one-pot sulfonium-mediated synthesis of homo- and heterodimeric pyrroloindolines 140 was developed by combination of DMSO and Tf 2 O (Scheme 17b ). 33d Intramolecular cyclization of tryptamine with DMSO/Tf 2 O, followed by substitution with indoles or anilines, produced C3a-nitrogen-linked pyrroloindolines, including several bioactive alkaloids.…”

Section: Electrophilic Alkylation Using Alkylsulfonium Saltsmentioning

confidence: 99%

“…33 In 2011, Kawasaki and co-workers reported the sulfonium-mediated functionalization of indole derivatives 131 with methanol at the 2α-position in the presence of sulfoxide and trifluoroacetic anhydride (Scheme 17a ). 33` b c The active thionium species 134 were derived in situ from the alkyl or aryl sulfoxide and TFAA. In addition to methanol, other carbon- and heteroatom-nucleophiles 132 were also directly introduced into 131 to form 133 in excellent yields.…”

Section: Electrophilic Alkylation Using Alkylsulfonium Saltsmentioning

confidence: 99%

Alkylation Reactions with Alkylsulfonium Salts

Tian

Zhang

2021

Synthesis

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Application of alkylsulfonium salts as alkyl transfer reagents in organic synthesis has reemerged over the past years. Numerous heteroatom- and carbon-centered nucleophiles, alkenes, arenes, alkynes, organometallic reagents, and others were readily alkylated by alkylsulfonium salts under mild conditions. The reactions feature convenience, high efficiency, readily accessible and structurally diversified alkylation reagents, good functional group tolerance, and a wide range of substrate types, allowing for facile synthesis of various useful organic molecules from the commercially available building blocks. This review summarizes the alkylation reactions using either isolated or in situ formed alkylsulfonium salts via nucleophilic substitution, transition-metal-catalyzed reactions, and photoredox processes.

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“…through twofold CÀHf unctionalization to give benzothiophene products.T he method is particularly useful for the direct construction of important polyaromatic benzothiophenes. [3] Thef irst stage of this process relies on an intermolecular interrupted Pummerer reaction [18,19] between an activated sulfoxide, 2a,and an arene 1a. (Figure 1, i).…”

mentioning

confidence: 99%

Metal‐Free Synthesis of Benzothiophenes by Twofold C−H Functionalization: Direct Access to Materials‐Oriented Heteroaromatics

et al. 2019

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Due to their ubiquity in nature and frequent use in organic electronic materials,b enzothiophenes are highly sought after.H ere we set out an unprecedented procedure for the formation of benzothiophenes by the twofold vicinal CÀH functionalization of arenes that does not require metal catalysis.T his one-pot annulation proceeds through an interrupted Pummerer reaction/[3,3]-sigmatropic rearrangement/ cyclization sequence to deliver various benzothiophene products.T he procedure is particularly effective for the rapid synthesis of benzothiophenes from non-prefunctionalized polyaromatic hydrocarbons (PAHs).

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Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position

Cited by 29 publications

References 63 publications

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Alkylation Reactions with Alkylsulfonium Salts

Metal‐Free Synthesis of Benzothiophenes by Twofold C−H Functionalization: Direct Access to Materials‐Oriented Heteroaromatics

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