55262-12-9Relevant academic research and scientific papers
Functionalized Allyl Aryl Ether Synthesis from Benzoic Acids Using a Dearomatization and Decarboxylative Allylation Approach
Hsieh, Cheng-En,Jiang, Yu-Min,Chou, Chih-Ming
supporting information, p. 653 - 665 (2019/01/24)
A strategy toward the preparation of substituted allyl aryl ethers from benzoic acids via a dearomatization and decarboxylative allylation (DcA) reaction is presented. The benzoic acids undergo a dearomatization to give alkylated 2,5-cyclohexadienyl ketoesters which are subjected to a palladium-catalyzed DcA reaction, providing a variety of functionalized allyl aryl ethers. In addition, the combination of a resonance stabilized DcA reaction with a Claisen rearrangement for the synthesis of multisubstituted phenols and applying to dihydroplicatin B derivative synthesis is also presented.
Palladium-Catalyzed Decarboxylative γ-Olefination of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Vinyl Halides
Chang, Chi-Hao,Chou, Chih-Ming
supporting information, p. 1949 - 1952 (2018/04/16)
This study explores a Pd-catalyzed decarboxylative Heck-type Csp3-Csp2 coupling reaction of 2,5-cyclohexadiene-1-carboxylic acid derivatives with vinyl halides to provide γ-olefination products. The olefinated 1,3-cyclohexadienes can be further oxidized to produce meta-alkylated stilbene derivatives. Additionally, the conjugated diene products can also undergo a Diels-Alder reaction to produce a bicyclo[2.2.2]octadiene framework.
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.
