Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 44, Pages 12082-12091Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901774
Keywords
alkylation; aromatic compounds; Birch reduction; carboxylic acids; decarbonylation
Categories
Funding
- University of Potsdam
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available