Towards tetrasubstituted furans through rearrangement and cyclodimerization of acetylenic ketones

Dai, Zhenyun; Xu, Chenyong; Tian, Rongqiang; Duan, Zheng

doi:10.1039/d3ob02036c

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob02036c

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Towards tetrasubstituted furans through rearrangement and cyclodimerization of acetylenic ketones

Zhenyun Dai,

Chenyong Xu,

Rongqiang Tian

et al.

Abstract: A cyclodimerization of readily accessible acetylenic ketones facilitated by phosphane-borane complex under base is achieved. This methodology allows one pot synthesis of phosphorus-involved tetrasubstituted furans via the construction of a...

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2024

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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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show abstract

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Towards tetrasubstituted furans through rearrangement and cyclodimerization of acetylenic ketones

Abstract: A cyclodimerization of readily accessible acetylenic ketones facilitated by phosphane-borane complex under base is achieved. This methodology allows one pot synthesis of phosphorus-involved tetrasubstituted furans via the construction of a...

Cited by 1 publication

References 54 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

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