Ti(OiPr)4-Facilitated Formal Deoxygenative Annulation of Alkynyl 1,2-Diketones for the Synthesis of Highly Functionalized Furans

Lan, Shouang; Liu, Rui; Kong, Xiangbin; Liu, Jinggong; Luo, Benlong; Yang, Shuang; Fang, Xinqiang

doi:10.1021/acs.orglett.1c00291

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2022

2024

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Cited by 5 publications

References 66 publications

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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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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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Five-membered ring systems: furans and benzofurans

Kwiecień

2023

Progress in Heterocyclic Chemistry

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Titanium-Mediated Domino Cross-Coupling/Cyclodehydration and Aldol-Addition/Cyclocondensation: Concise and Regioselective Synthesis of Polysubstituted and Fused Furans

et al. 2022

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Titanium enolates, in situ-generated from readily available ketones and titanium tetraisopropoxide, undergo domino cross-coupling/cyclodehydration or domino Aldol-addition/cyclocondensation with α-chloroketones to provide synthetically valuable furan derivatives. The domino process tolerates a variety of cyclic and acyclic ketones and chloroketones, producing polysubstituted furans and bi-, tri-, and tetracyclic fused furans.

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Ti(OⁱPr)₄-Facilitated Formal Deoxygenative Annulation of Alkynyl 1,2-Diketones for the Synthesis of Highly Functionalized Furans

Cited by 5 publications

References 66 publications

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

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

Five-membered ring systems: furans and benzofurans

Titanium-Mediated Domino Cross-Coupling/Cyclodehydration and Aldol-Addition/Cyclocondensation: Concise and Regioselective Synthesis of Polysubstituted and Fused Furans

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