Direct α-Arylation of Benzo[b]furans Catalyzed by a Pd3 Cluster

被引:8
作者
Yao, Jian [1 ,2 ]
Shao, Lili [2 ]
Kang, Xi [3 ,4 ]
Zhu, Manzhou [3 ,4 ]
Huo, Xiaohong [1 ]
Wang, Xiaoming [2 ,5 ]
机构
[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth,State Key Lab Organometal, Shanghai 200032, Peoples R China
[3] Anhui Univ, Dept Chem, Hefei 230601, Peoples R China
[4] Anhui Univ, Ctr Atom Engn Adv Mat, Hefei 230601, Peoples R China
[5] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
BIOACTIVE BENZOFURAN DERIVATIVES; C-H FUNCTIONALIZATION; REGIOSELECTIVE C-2 ARYLATION; BETA-AMYLOID PLAQUES; BOND ARYLATION; PALLADIUM CLUSTERS; INTERNAL ALKYNES; SEMI-REDUCTION; THIOPHENES; COMPLEXES;
D O I
10.1021/acs.joc.3c02428
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
As an interim paradigm for the catalysts between those based on more conventional mononuclear molecular Pd complexes and Pd-n nanoparticles widely used in organic synthesis, polynuclear palladium clusters have attracted great attention for their unique reactivity and electronic properties. However, the development of Pd cluster catalysts for organic transformations and mechanistic investigations is still largely unexploited. Herein, we disclose the use of trinuclear palladium (Pd3Cl) species as an active catalyst for the direct C-H alpha-arylation of benzo[b]furans with aryl iodides to afford 2-arylbenzofurans in good yields under mild conditions. With this method, broad substrate adaptability was observed, and several drug intermediates were synthesized in high yields. Mechanistic studies indicated that the Pd-3 core most likely remained intact throughout the reaction course.
引用
收藏
页码:1719 / 1726
页数:8
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