104-62-1Relevant articles and documents
Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles
Kamijo, Shin,Huo, Zhibao,Jin, Tienan,Kanazawa, Chikashi,Yamamoto, Yoshinori
, p. 6389 - 6397 (2005)
Two facile deallylation protocols have been developed for the preparation of N-unsubstituted triazoles and tetrazoles. The first protocol is a direct deallylation using a combination of a catalytic amount of nickel complex, NiCl2(dppe), and a stoichiometric amount of Grignard reagent, tBuMgCl. The second protocol is a stepwise deallylation through consecutive reactions of isomerization and ozonolysis. The isomerization from N-allylazoles to N-vinylazoles is catalyzed by a ruthenium complex, HRuCl(CO)(PPh3)3, and the following ozonolysis of the derived N-vinyl intermediates affords N-unsubstituted azoles. These protocols can be used complementarily depending on the type of functional groups in the parent allylated azoles.
Polyvinylpolypyrrolidoniume tribromide as new and metal-free catalyst for the formylation and trimethylsilylation of hydroxyl group
Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Zamani, Parisa
, p. 1207 - 1210 (2011)
Trimethylsilylation of alcohols was achieved using 1,1,1,3,3,3- hexamethyldisilazane (HMDS) as silylating agent, in the presence of polyvinylpolypyrrolidoniume tribromide in acetonitrile at room temperature. Also a variety of alcohols were converted into alkyl formates by ethyl formate and a catalytic amount of polyvinylpolypyrrolidoniume tribromide under solvent free conditions at room temperature.
Tandem Acid/Pd-Catalyzed Reductive Rearrangement of Glycol Derivatives
Ciszek, Benjamin,Fleischer, Ivana,Kathe, Prasad,Schmidt, Tanno A.
, p. 3641 - 3646 (2020/03/25)
Herein, we describe the acid/Pd-tandem-catalyzed transformation of glycol derivatives into terminal formic esters. Mechanistic investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2] hydrogen migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. Whereas the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising a PdII or Pd0 precursor in loadings as low as 0.75 mol % and α,α′-bis(di-tert-butylphosphino)-o-xylene as ligand. The reduction step makes use of formic acid as an easy-to-handle transfer reductant. The substrate scope of the transformation encompasses both aromatic and aliphatic substrates and a variety of leaving groups.
Sustainable Co-Synthesis of Glycolic Acid, Formamides and Formates from 1,3-Dihydroxyacetone by a Cu/Al2O3 Catalyst with a Single Active Sites
Dai, Xingchao,Adomeit, Sven,Rabeah, Jabor,Kreyenschulte, Carsten,Brückner, Angelika,Wang, Hongli,Shi, Feng
supporting information, p. 5251 - 5255 (2019/03/07)
Glycolic acid (GA), as important building block of biodegradable polymers, has been synthesized for the first time in excellent yields at room temperature by selective oxidation of 1,3-dihyroxyacetone (DHA) using a cheap supported Cu/Al2O3 catalyst with single active CuII species. By combining EPR spin-trapping and operando ATR-IR experiments, different mechanisms for the co-synthesis of GA, formates, and formamides have been derived, in which .OH radicals formed from H2O2 by a Fenton-like reaction play a key role.