Gold‐Catalyzed Intramolecular Carbothiolation of Alkynes: Synthesis of 2,3‐Disubstituted Benzothiophenes from (α<i>‐</i>Alkoxy Alkyl) (<i>ortho</i>‐Alkynyl Phenyl) Sulfides

Nakamura, Itaru; Sato, Takuma; Yamamoto, Yoshinori

doi:10.1002/anie.200601178

Cited by 325 publications

(93 citation statements)

References 35 publications

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“…However, Yamamoto described the attack of the sulfur atom of aryl thioethers to afford benzothiophenes (equation 31). 152 More recently, it has been showed that propargylic thioethers or thioacetals undergo migration to give carbenes that cyclize in hydroarylation processes 153 and thiocarbamates that evolve by propargylic rearrangement. 154 Thiosilanes can perform as both sulfur nucleophiles and silicon electrophiles in intramolecular reactions to afford benzothiophenes (equation 32).…”

Section: Sulfur Nucleophilesmentioning

confidence: 99%

Gold in Homogeneous Catalysis

Jim��nez-N��ez¹,

Echavarren²

2005

Encyclopedia of Inorganic Chemistry

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Section: Sulfur Nucleophilesmentioning

confidence: 99%

Gold in Homogeneous Catalysis

Jim��nez-N��ez¹,

Echavarren²

2005

Encyclopedia of Inorganic Chemistry

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“…Gold-catalyzed cyclization of -alkoxyalkyl(ortho-alkynylphenyl)sulfides gave 2,3-disubstituted benzothiophenes in excellent yields. 89 Similarly, gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes gave 3-silyl-substituted benzothiophenes. Gold-catalyzed and/or copper-catalyzed benzannulation reactions between orthoalkynylbenzaldehydes 22 and alkynes gave naphthyl carbonyl compounds 23 in high to good yields (Scheme 7).…”

Section: Scheme 5 Indene Synthesis Via C-o Bond Additionmentioning

confidence: 99%

π-Conjugated carbocycles and heterocycles via annulation through C-H and X-Y activation across CC triple bonds

Yamamoto¹,

Almansour²,

Arumugam³

et al. 2015

Arkivoc

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AbstractIn this account our own research results on the methods of annulation and hetero-annulation across alkynes are summarized, especially emphasizing the annulation and hetero-annulation through C-H and X-Y activation. A wide range of quinolines, isoquinolines, indoles, benzofurans, indenes, and benzothiophenes can be synthesized via mono-annulation of ortho-alkynylaryl derivatives using transition metal catalysts and/or iodine reagents. Benzocarbazoles, benzonaphthothiophenes, and indenochromenes can be synthesized via cascade annulation of 1,2-dialkynyl substituted benzene derivatives. Palladium-catalyzed crossover annulation of compounds bearing two vicinal CC triple bonds attached to an unsaturated ring gives dibenzopentalenes through C-H activation, and intramolecular cross annulation of bisbiarylalkynes affords 9,9-bifluorenylidenes via dual C-H activation.

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“…Indeed, the method represents a thiophene skeleton, which would provide a more efficient and practical route, are extremely rare in the literature presumably because of catalyst poisoning by sulfur. Only a few reports in which gold 57) or palladium 58) catalysts have been used to effect C-S bond formation have appeared.…”

Section: -46)mentioning

confidence: 99%

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

Inamoto

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

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Gold‐Catalyzed Intramolecular Carbothiolation of Alkynes: Synthesis of 2,3‐Disubstituted Benzothiophenes from (α‐Alkoxy Alkyl) (ortho‐Alkynyl Phenyl) Sulfides

Cited by 325 publications

References 35 publications

Gold in Homogeneous Catalysis

Gold in Homogeneous Catalysis

π-Conjugated carbocycles and heterocycles via annulation through C-H and X-Y activation across CC triple bonds

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

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