Ring-Opening Ortho-C-H Allylation of Benzoic Acids with Vinylcyclopropanes: Merging Catalytic C-H and C-C Activation Concepts

被引：31
|
作者：
Hu, Zhiyong [1 ]
Hu, Xiao-Qiang [1 ]
Zhang, Guodong [1 ]
Goossben, Lukas J. [1 ]
机构：
[1] Ruhr Univ Bochum, Lehrstuhl Organ Chem 1, Univ Str 150, D-44801 Bochum, Germany
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 17期
关键词：
CARBOXYLIC-ACIDS; BOND FUNCTIONALIZATION; HYDROARYLATION; ARYLATION; ALKYNES; CYCLOPROPENES; ROUTES; ARENES; SP(2);
D O I：
10.1021/acs.orglett.9b02393
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Ru-catalyzed selective and atom-economic ortho-C-H allylation of aromatic acids with vinylcyclopropanes is reported. The reaction proceeds with selective cleavage of both a C-H and a C-C bond. A wide range of allylarenes were synthesized in high yields and stereoselectivities. The vinylcyclopropane substrates can optionally be generated in situ from a diazo compound and 1,3-butadiene. Concise syntheses of isocoumarin and 3,4-dihydroisocoumarin derivatives underline the synthetic utility of the reaction.
引用
收藏
页码：6770 / 6773
页数：4
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