6640-85-3Relevant articles and documents
Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols
Li, Yahui,Wang, Changsheng,Zhu, Fengxiang,Wang, Zechao,Dixneuf, Pierre H.,Wu, Xiao-Feng
, p. 1341 - 1345 (2017/04/14)
Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the C sp3 ?H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.
1,4-Bis-Dipp/Mes-1,2,4-Triazolylidenes: Carbene Catalysts That Efficiently Overcome Steric Hindrance in the Redox Esterification of α- And β-Substituted α,β-Enals
Yatham, Veera Reddy,Harnying, Wacharee,Kootz, Darius,Neud?rfl, J?rg-M.,Schl?rer, Nils E.,Berkessel, Albrecht
supporting information, p. 2670 - 2677 (2016/03/12)
As reported by Scheidt and Bode in 2005, sterically nonencumbered α,β-enals are readily converted to saturated esters in the presence of alcohols and N-heterocyclic carbene catalysts, e.g., benzimidazolylidenes or triazolylidenes. However, substituents at the α- or β-position of the α,β-enal substrate are typically not tolerated, thus severely limiting the substrate spectrum. On the basis of our earlier mechanistic studies, a set of N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts were synthesized and evaluated as (pre)catalysts in the redox esterification of various α- or β-substituted enals. In particular the 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes overcome the above limitations and efficiently catalyze the redox esterification of a whole series of α/β-substituted enals hitherto not amenable to NHC-catalyzed transformations. The synthetic value of 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes is further demonstrated by the one-step bicyclization of 10-oxocitral to (racemic) nepetalactone in diastereomerically pure form.
Esterification of Carboxylic Acids by Alcohols with 2-Chloro-1,3,5-trinitrobenzene as Condensing Agent
Takimoto, Seiji,Inanaga, Junji,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 1470 - 1473 (2007/10/02)
When mixtures of carboxylic acids or their sodium salts and alcohols were treatment with 2-chloro-1,3,5-trinitrobenzene in the presence of pyridine under mild conditions, the corresponding carboxylic esters were formed.The yields and the rates of the ester formation depended on the types of the acids and the alcohols used.