50919-60-3Relevant academic research and scientific papers
Synthesis of phthalic acid derivatives: Via Pd-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates
Liao, Gang,Chen, Hao-Ming,Shi, Bing-Feng
, p. 10859 - 10862 (2018/10/02)
A Pd(ii)-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates has been developed. A broad range of benzamides and alkyl chloroformates are compatible with this protocol. The reaction is operationally simple and scalable. The direct group could be readily removed to access substituted phthalic acid esters (PAEs), 1,2-dibenzyl alcohols and phthalamides. Besides alkoxycarbonylation of benzamide β-C-H bonds, γ-alkoxycarbonylation of 2-phenylacetamide is also feasible.
Practical three-component synthesis of crowded arenes with donor-acceptor substitution
Fichtler, Robert,Neudoerfl, Joerg-M.,Jacobi Von Wangelin, Axel
scheme or table, p. 7224 - 7236 (2011/11/04)
An operationally simple two-step synthesis of substituted anilides has been developed. The methodology utilizes carboxamides, aldehydes, and olefins (or alkynes) as cheap starting materials and relies upon the sequential combination of condensation, cyclo
Unusual coupling reactions of aldehydes and alkynes: A novel preparation of substituted phthalic acid derivatives by automated synthesis
Von Wangelin, Axel Jacobi,Neumann, Helfried,Goerdes, Dirk,Klaus, Stefan,Jiao, Haijun,Spannenberg, Anke,Krueger, Thomas,Wendler, Christian,Thurow, Kerstin,Stoll, Norbert,Beller, Matthias
, p. 2273 - 2281 (2007/10/03)
Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from α,β-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels-Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation - cycloadditionelimination sequence has been applied to a variety of α,β-unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4-syn elimination pathway under standard conditions.
