钯催化1,6-烯炔的环化反应研究

doi:10.6023/cjoc202401032

综述与进展

钯催化1,6-烯炔的环化反应研究

刘雯娟^a, 陈品红^*,a,b

^a上海理工大学材料与化学学院上海 200093;
^b中国科学院上海有机化学研究所金属有机化学国家重点实验室沪港化学合成联合实验室分子合成科学卓越创新中心中国科学院大学上海 200032

收稿日期:2024-01-26 修回日期:2024-03-05
基金资助:
国家重点研发计划(No. 2021YFA1500100)、国家自然科学基金(Nos. 22171279, 22331012)、中国科学院青年创新促进会(No. Y2022074)资助项目.

Palladium-Catalyzed Cyclization of 1,6-Enynes

Liu Wenjuan^a, Chen Pinhong^*,a,b

^aSchool of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093;
^bState Key Laboratory of Organometallic Chemistry and Shanghai Hong Kong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032

Received:2024-01-26 Revised:2024-03-05
Contact: *E-mail: pinhongchen@mail.sioc.ac.cn
Supported by:
National Key R&D Program of China (No. 2021YFA1500100), the National Natural Science Foundation of China (Nos. 22171279, 22331012), and the Youth Innovation Promotion Association of Chinese Academy of Sciences (No. Y2022074).

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摘要/Abstract

官能化的碳环或杂环结构广泛存在于天然产物及其他生物活性分子中, 是一类极具合成价值的重要骨架. 而1, n-烯炔的环化反应是构建官能化的碳环或杂环化合物的最具原子经济性, 且高效的方法之一, 其中钯催化的1,6-烯炔的环化反应研究较为成熟, 取得了一系列重要进展. 本文聚焦于由炔烃亲核钯化启动的1,6-烯炔的环化反应, 按照炔烃的亲核钯化方式包括氢钯化、碳钯化、卤钯化和氧钯化等分类, 系统介绍近二十年内钯催化1, 6-烯炔的环化反应进展, 尤其是不对称催化反应, 探讨了反应的机理, 并展望了该领域今后发展的方向.

关键词: 钯催化, 1,6-烯炔, 环化反应, 亲核钯化, 碳环化合物, 杂环化合物

Functionalized carbo- and hetero-cyclic compounds are widely found in natural products and other bioactive molecules, which are also important scaffolds with significant synthetic value. The cyclization of 1, n-enynes is one of the most atom-economic and efficient approaches. In particular, palladium-catalyzed cyclization of 1,6-enynes has been extensively studied and has achieved significant advancements. This review focuses on the cyclization of 1,6-enynes initiated by nucleopalladation of alkynes, including hydropalladation, carbopalladation, halopalladation and oxypalladation. It was classified by the nucleopalladation and systematically summarized the recent developments in palladium-catalyzed 1, 6-enyne cyclization over the past two decades. Special emphasis was placed on the asymmetric reactions, and reaction mechanisms, along with further prospects of this field.

Key words: Palladium catalysis, 1,6-enynes, cyclization reaction, nucleopalladation, carbocyclic compounds, heterocyclic compounds

引用此文

刘雯娟, 陈品红. 钯催化1,6-烯炔的环化反应研究[J]. 有机化学, doi: 10.6023/cjoc202401032.

Liu Wenjuan, Chen Pinhong. Palladium-Catalyzed Cyclization of 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202401032.

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