ChemInform Abstract: Gold(I)‐Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylation of Arenes.

Cuenca, Ana B.; Montserrat, Sergi; Hossain, Khondoker Mokaddem; Mancha, Gisela; Lledós, Agustı́; Medio‐Simón, Mercedes; Ujaque, Gregori; Asensio, Gregorio

doi:10.1002/chin.201012084

Cited by 2 publications

(2 citation statements)

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“…118 The first intermolecular variants of this transformation were reported by the Liu and Asensio groups, providing access to acyclic αaryl ketones (187) (Scheme 33b). 119,120 In lieu of catalytic activation using gold, alkyne derivatives can also be competently activated by simple Brønsted acids to afford electrophilic intermediates suited for sulfoxide attack (Scheme 34). In 2014, Maulide and co-workers reported the formation of arylated amide derivatives (191) through transient formation of keteniminium ions (190) from ynamides (Scheme 34a).…”

Section: Sigmatropic Rearrangements Of Activated 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: Sigmatropic Rearrangements Of Activated 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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“…Alternatively, vinyl gold species I could undergo a sulfonium [3,3]-sigmatropic rearrangement (charge-accelerated thio-Claisen rearrangement), 14 to give cation III, the latter then affords the final product via rearomatization and protodeauration (pathway B). Initial reports on the gold-catalyzed conversion of alkynyl sulfoxides assumed the mechanism to proceed intermolecularly, forming the α-imino gold carbene, 15 whereas later experimental and theoretical studies, carried out by Asensio et al 16 and Zhang et al, 17 The reactions were run on a 21.8 μmol scale in 0.5 mL of toluene in the presence of 5.00 mol % of the gold catalyst and 5.00 mol % of the silver salt. The yield was determined by 1 H NMR spectroscopy using hexamethylbenzene as the internal standard.…”

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confidence: 99%

Gold-Catalyzed [3,3]-Sigmatropic Rearrangement of ortho-Alkynyl-S,S-diarylsulfilimines

et al. 2023

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Highly functionalized 5H-pyrrolo[2,3-b]pyrazine cores, carrying a diaryl sulfide moiety at the C-7 position, were obtained from a gold-catalyzed reaction using easily accessible ortho-alkynyl-substituted S,Sdiarylsulfilimines as intramolecular nitrene transfer reagents for the first time. The reaction proceeds under mild conditions, providing excellent yields while tolerating a large variety of different substitution patterns. We provide experimental evidence for an intramolecular reaction mechanism, likely including an unprecedented gold-catalyzed amino sulfonium [3,3]sigmatropic rearrangement.

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ChemInform Abstract: Gold(I)‐Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylation of Arenes.

Cited by 2 publications

References 1 publication

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

Gold-Catalyzed [3,3]-Sigmatropic Rearrangement of ortho-Alkynyl-S,S-diarylsulfilimines

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