AgOTf/I2-Mediated Cyclization/Cross-Coupling/Isomerization of Enynones with Phosphorus Ylides: An Expedient Route to Stereoselective Synthesis of (E)-2-Alkenylfurans

Tang, Ling; Zhang, Yangyi; Deng, Guoliang

doi:10.1021/acs.joc.1c01109

Cited by 12 publications

(1 citation statement)

References 25 publications

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“…After the formation of furyl silver carbene I via intramolecular 5-exo-dig cyclization, a nucleophilic attack by iodo- Similarly, phosphorus ylides 66 are viable in silver-catalyzed cross-coupling reaction with furyl metal carbenes I, derived from enynones 1, producing (E)-2-alkenylfurans 64 (Scheme 24B). [36] Furyl metal carbene I, formed from arylsubstituted enynone 1, undergoes cross-coupling with phosphorus ylide 66, generating zwitterionic intermediate II.…”

Section: Cross-coupling With Ylides/elimination Cascade Reactionmentioning

confidence: 99%

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Cho,

Kim

2024

Asian J Org Chem

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Enynones and enynals represent donor‐type carbene precursors that efficiently form furyl metal carbenes via a catalytic intramolecular 5‐exo‐dig cyclization and rearrangement cascade, in a 100% atom‐economical manner, using various metals. These furyl metal carbenes have been successfully utilized in numerous carbene reactions, including metal carbene X–H insertion, cyclopropanations, metathesis, and cross‐coupling, demonstrating a broad reaction scope and efficiency in constructing highly functionalized furans. Recent years have witnessed significant advancements in transformations involving furyl metal carbenes, especially in asymmetric carbene insertion reactions, domino reactions involving zwitterionic intermediates, various rearrangement strategies, and their application in synthesizing functional materials and drug candidates. In this review, we summarize recent progress in furyl metal carbene reactions generated from enynones and enynals, focusing on the synthesis of highly functionalized furans.

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Section: Cross-coupling With Ylides/elimination Cascade Reactionmentioning

confidence: 99%

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Cho,

Kim

2024

Asian J Org Chem

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Synthesis of Functionalized Furans: Three‐Component Reactions Involving Ketene Dithioacetals, Acetylenes, and Phosphines to Generate Phosphorus Ylides or N‐Acyliminophosphoranes

Zhai,

Yan,

Liu

et al. 2024

Adv Synth Catal

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Synthesis of new polysubstituted furans incorporating reactive phosphorus ylides or N‑acyliminophosphoranes was achieved by the heterocyclization of flexible α‐acyl ketene dithioacetals. This one‐pot tandem reaction was initiated by acyl‐directed desulfurative Sonogashira coupling, followed by 1,6‐addition of phosphine to the in situ‐generated enynone and subsequent 5‐exo‐dig cyclization, as well as phosphoranation. The selectivity toward the two products, i.e. α‐phosphorus ylides vs. α‐N‑acyliminophosphoranes‐substituted furans, was determined by both electron‐deficient acetylenes and copper salts.

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Superbase‐Catalyzed Steric‐Hindrance‐Induced Dimerization of Alkynones to Highly Functionalized Furans

et al. 2023

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The cascade dimerization of alkynones bearing sterically hindered secondary alkyl groups at the carbonyl function has unexpectedly furnished highly functionalized furans. The reaction efficiently occurs in the presence of potassium tert‐butoxide/dimethylsulfoxide superbase catalytic system at room temperature. Alkynones having additional C−H active site at the carbon‐carbon triple bond have followed another dimerization pathway to afford 3‐alkenylpyran‐4‐ones. The discovery of these reactions expands the traditional knowledge about the reactivity of alkynones in strong basic medium.

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AgOTf/I₂-Mediated Cyclization/Cross-Coupling/Isomerization of Enynones with Phosphorus Ylides: An Expedient Route to Stereoselective Synthesis of (E)-2-Alkenylfurans

Cited by 12 publications

References 25 publications

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Synthesis of Functionalized Furans: Three‐Component Reactions Involving Ketene Dithioacetals, Acetylenes, and Phosphines to Generate Phosphorus Ylides or N‐Acyliminophosphoranes

Superbase‐Catalyzed Steric‐Hindrance‐Induced Dimerization of Alkynones to Highly Functionalized Furans

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