Access to 4-Alkenylated Coumarins via Ruthenium-Catalyzed Olefinic C-H Alkenylation of Coumarins with Modifiable and Removable Directing Groups

被引:26
|
作者
Wang, Yu-Jiao [1 ]
Wang, Tong-Tong [1 ]
Yao, Lan [1 ]
Wang, Qian-Long [1 ]
Zhao, Li-Ming [1 ,2 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
[2] Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 15期
关键词
CYCLOADDITION REACTIONS; COUPLING REACTION; CROSS-COUPLINGS; DERIVATIVES; FUNCTIONALIZATION; OLEFINATION; ACTIVATION; ALKENES; DESIGN; ROUTE;
D O I
10.1021/acs.joc.0c00249
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ruthenium-catalyzed activation of the C4 position of coumarins for coupling with acrylates was described using modifiable ketone as a directing group. The alkenylation reaction provided a direct approach to prepare previously inaccessible 4-alkenylated coumarins with operational simplicity and high atom-economy. This protocol also worked well with coumarin-3-carboxylic acids to unveil a rare instance of a tandem alkenylation/decarboxylation reaction. The potential value of this approach was further highlighted by the efficient synthesis of several heterocyclic fused coumarin derivatives.
引用
收藏
页码:9514 / 9524
页数:11
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