Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-10-16 DOI:10.1021/acscatal.4c04956

Changhua Song, Shouyun Yu

引用次数: 0

Abstract

A photoexcited palladium-catalyzed synthesis of chiral allenes from alkynes via a sequence of isomerization and deracemization is disclosed. This method offers an efficient and cost-effective approach to produce a wide range of chiral allenes with good enantioselectivities and yields (up to 98% yield and 99% ee). The use of readily available and stable alkynes as starting materials simplifies experimental procedures and broadens the scope of the chiral allene synthesis. DBU plays a crucial dual role in this reaction to effectively facilitate the isomerization of alkynes to allenes and enhance the palladium-catalyzed deracemization under visible light excitation, both of which are vital for the success of the process.

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光激发钯催化通过异构化和脱芳香化顺序从炔烃合成手性烯烃

本发明公开了一种光激发钯催化合成手性烯烃的方法，该方法通过一连串的异构化和衍生化过程从炔烃中合成手性烯烃。该方法提供了一种高效、低成本的方法来生产各种手性烯烃，并具有良好的对映选择性和收率（收率高达 98%，ee 为 99%）。使用容易获得且稳定的炔烃作为起始材料，简化了实验程序，扩大了手性烯烃合成的范围。DBU 在该反应中发挥了至关重要的双重作用，它有效地促进了炔烃向烯烃的异构化，并在可见光激发下增强了钯催化的反空化作用，而这两者对于该过程的成功都至关重要。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.