The Ketene‐Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers

Zhang, Wenhan; Ready, Joseph M.

doi:10.1002/anie.201405036

Cited by 26 publications

(17 citation statements)

References 44 publications

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“…22 In parallel, tert -butyl indolyl ynol ether 20 was synthesized according to the Sonogashira coupling condition that we reported previously. 13 Dichloromethane was added as co-solvent to improve the solubility of the starting material 19 , 23 and a 75% yield of the benzene sulfonamide (Bs) protected indole 20 was obtained.…”

Section: Resultsmentioning

confidence: 99%

A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks

Zhang

Ready

2016

J. Am. Chem. Soc.

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We report a concise total synthesis of dictyodendrin F and the first total syntheses of dictyodendrins H and I in six steps. In these syntheses, aryl ynol ethers were employed as the key building blocks to introduce aryl and heteroaryl rings in the dictyodendrins. This rapid synthesis utilized a novel hetero-[2+2]-cycloaddition reaction between two aryl ynol ethers to yield a cyclobutenone ring. The cyclobutenone was sequentially converted into a highly substituted carbazole via a retro-4π/6π-electrocyclization-N-acylation cascade reaction to provide the dictyodendrin core. Consecutive intramolecular oxidative coupling and deprotection gave dictyodendrins F, H, and I.

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Section: Resultsmentioning

confidence: 99%

A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks

Zhang

Ready

2016

J. Am. Chem. Soc.

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“…Ready et al 14 acetylide allows for the activation of the imine (the nitrogen atom and an oxygen of the sulfoxide).…”

Section: Scheme 30mentioning

confidence: 99%

The chemistry of ynol and thioynol ethers

Gray

Wilden

2016

Org. Biomol. Chem.

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Alkynyl ethers and alkynyl thioethers ('ynol ethers' and 'thioynol ethers') are appealing building-blocks in synthetic chemistry due to their ease of manipulation and predictable reactivity. Until recently however, their potential has remained underexploited due to difficulties in preparation and isolation. Although recent advances in synthetic chemistry have highlighted various applications for ynol ethers, the equivalent thioynol examples have been rather less exploited despite a unique and fascinating reactivity profile. Although superficially the chemistry of alkynyl ethers and their sulfide counterparts are similar, close examination of their chemistry reveals important differences which can be exploited by the synthetic chemist. This review will examine the preparation of both classes of compound and examine their reactivity to highlight their powerful synthetic applications. Particular focus will be made of thiynol ethers whose chemistry exhibits some fascinating differences compared to their oxygen counterparts and have immense untapped potential for synthetic chemistry.

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“…This palladacycle contains an imino moiety and represents a new class of C , C ‐palladacycles, and can be utilized to develop synthetically useful reactions, in particular for N ‐containing heterocycles. However, this C , C ‐palladacycle has not been exploited to develop other organic reactions ,,. On the other hand, the Shi group demonstrated that diaziridinone exhibits high reactivity towards C , C ‐palladacycles (Scheme ) ,.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzimidazoles through Palladium‐Catalyzed Amination of 2‐Iodobenzimines with Diaziridinone

et al. 2018

Adv Synth Catal

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An efficient approach for the synthesis of benzimidazoles has been developed through the Pdcatalyzed amination of 2-iodobenzimines with diaziridinone. A wide range of 2-(hetero)aryl benzimidazloes are synthesized in good to excellent yields. The reactions likely involve C,C-palladacycles derived from 2iodobenzimines as the key intermediate, and the palladacycles reacted with diaziridinone to form benzimidazoles.

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The Ketene‐Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers

Cited by 26 publications

References 44 publications

A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks

A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks

The chemistry of ynol and thioynol ethers

Synthesis of Benzimidazoles through Palladium‐Catalyzed Amination of 2‐Iodobenzimines with Diaziridinone

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