Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany.
Chemistry. 2009 Nov 9;15(44):12082-91. doi: 10.1002/chem.200901774.
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.
各种带有不同烷基侧链的芳烃以高产率和优异的区域选择性合成。以甲苯酸和萘酸为起始原料，通过伯奇还原和随后的脱羧反应，方便地将羧基转化为卤代烷烃。该方法的特点是起始原料和试剂价格低廉，并实现了芳烃的甲基化。除了简单的烷基取代基外，通过苄基、氟、氨基和酯基，芳烃的官能团化范围得到了扩展。通过添加叔丁醇，我们能够在伯奇还原过程中控制 1-萘酸的烷基化。这使得可以从相同的起始原料中区域选择性地合成单取代和双取代的萘。
