区域选择性
烷基
化学
烷基化
羧酸盐
表面改性
试剂
卤化物
有机化学
药物化学
催化作用
物理化学
作者
Tobias Krüger,Katja Vorndran,Torsten Linker
标识
DOI:10.1002/chem.200901774
摘要
Arenes with various alkyl side-chains were synthesized in high yields and excellent regioselectivities. Starting from toluic and naphthoic acids, the carboxylate group was conveniently substituted by alkyl halides by Birch reduction and subsequent decarbonylation. The method is characterized by inexpensive starting materials and reagents, and methylation of arenes was realized. Besides simple alkyl substituents, the scope of arene functionalization was extended by benzyl, fluoro, amino, and ester groups. We were able to control the alkylation of 1-naphthoic acid during Birch reduction by the addition of tert-butanol. This allowed the regioselective synthesis of mono and bis-substituted naphthalenes from the same starting material.
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