31689-43-7Relevant academic research and scientific papers
Diastereoselective hydroformylation of 2,5-cyclohexadienyl-1-carbinols with catalytic amounts of a reversibly bound directing group
Usui, Ippei,Nomura, Kenichi,Breit, Bernhard
supporting information; experimental part, p. 612 - 615 (2011/04/26)
A phosphinite plays a role as a reversibly bound directing group for the regio-and diastereoselective hydroformylation of 2,5-cyclohexadienyl-1- carbinols. Of the two alkene functions only one was functionalized through hydroformylation to form a syntheti
Regioselective arene functionalization: Simple substitution of carboxylate by alkyl groups
Krueger, Tobias,Vorndran, Katja,Linker, Torsten
experimental part, p. 12082 - 12091 (2010/05/17)
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.
Simple two-step ipso substitution of aromatic carboxylic acids by alkyl halides
Vorndran, Katja,Linker, Torsten
, p. 2489 - 2491 (2007/10/03)
Methyl-substituted arenes can be synthesized with high regioselectivity in only two steps through formal exchange of an aromatic carboxylic acid function with an alkyl substituent. The results obtained with toluic acid illustrate that good to very good yields can be obtained from inexpensive reagents (see scheme).
