Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins to synthesize skipped 1,4-dienes.

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI:10.1039/d5ob00173k

Cheng-Ping Shen, Hai-Tao Zhu, Guo-Hua Li, Xin Chang, Jia-Jun Xi, Ni-Ni Zhou, An-Xi Zhou

引用次数: 0

Abstract

A highly efficient method for the straightforward synthesis of skipped 1,4-dienes is presented via p-TsOH·H₂O-catalyzed intramolecular intercepted Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins in a one-pot manner. This cascade transformation is characterized by metal-free and mild conditions, extensive substrate applicability, atom economy, gram-scale production, and water as the sole by-product. Furthermore, the resulting functionalized 1,4-dienes could be derivatized by Fe(III)-promoted radical cyclization, allylic methoxylation under reductive conditions, and Pd(II)-catalyzed Sonogashira coupling.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.