The Ylide Dance: Base-Induced Furan Synthesis via Formal [3+2] Annulation of Phenacyl- and Alkenyl Sulfonium Salts

The Ylide Dance: Base-Induced Furan Synthesis via Formal [3+2] Annulation of Phenacyl- and Alkenyl Sulfonium Salts Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2025, Volume: 27, Number: 48, Pages: 13335-13339 Pages count : 5 DOI: 10.1021/acs.orglett.5c04395

Authors

Myasnikov Danil A. ¹ , Khodus Anastasia Y. ¹ , Mendogralo Elena Y. ¹ , Chabuka Beauty K. ² , Alabugin Igor V. ² , Trushkov Igor V. ³ , Uchuskin Maxim G. ¹

Affiliations

1	Perm State University, Bukireva st. 15, Perm, 614990, Russian Federation
2	Florida State University, Tallahassee, Florida 32306-4390, United States
3	N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation

A methodology for the synthesis of substituted furans via an “ylide dance” sequence has been developed. The reaction involves phenacyl sulfonium salts and alkenyl- or propargyl sulfonium salts under basic conditions. The key feature is a stepwise evolution where a primary sulfur ylide, generated from phenacyl sulfonium salt and base, transforms into another ylide, which then undergoes conversion into yet another, a “third generation” ylide, culminating in the formation of the target furan.

Myasnikov D.A. , Khodus A.Y. , Mendogralo E.Y. , Chabuka B.K. , Alabugin I.V. , Trushkov I.V. , Uchuskin M.G.
The Ylide Dance: Base-Induced Furan Synthesis via Formal [3+2] Annulation of Phenacyl- and Alkenyl Sulfonium Salts
Organic Letters. 2025. V.27. N48. P.13335-13339. DOI: 10.1021/acs.orglett.5c04395 WOS Scopus OpenAlex

Web of science:	WOS:001622009400001
Scopus:	2-s2.0-105024016471
OpenAlex:	W4416616413

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