文章基本信息

标题：Homologation of aryl ketones to long-chain ketones and aldehydes via C–C bond cleavage
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作者：Xing Wang ; Ling-Jun Li ; Zhen-Yu Wang 等
期刊名称：iScience
印刷版ISSN：2589-0042
出版年度：2022
卷号：25
期号：7
页码：1-40
DOI：10.1016/j.isci.2022.104505
语种：English
出版社：Elsevier
摘要：SummaryTransition metal-catalyzed C–C bond cleavage is a powerful tool for the reconstruction of a molecular skeleton. We report herein the multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes via ligand-promoted Ar−C(O) bond cleavage and subsequent cross coupling with alkenols. Various (hetero)aryl ketones are compatible in the reaction, affording the corresponding products wtih good to excellent yields with high regioselectivity. Further applications in the late-stage diversification of biologically important molecules demonstrate the synthetic utility of this protocol. Mechanistic studies indicate that the ligand plays an important role in both C–C bond cleavage and the asymmetric migration-insertion process.Graphical abstractDisplay OmittedHighlights•Ligand-promoted unstrained Ar–C(O) bond cleavage•Multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes•Late-stage diversification of drug and natural productChemistry; Organic chemistry; Organic synthesis