70423-45-9Relevant academic research and scientific papers
Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis
Lebedev, Yury,Polishchuk, Iuliia,Maity, Bholanath,Dinis Veloso Guerreiro, Miguel,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 19415 - 19423 (2019/12/24)
A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.
Facile one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridines by copper(II)-catalyzed oxidative N-N bond formation
Hirayama, Tasuku,Ueda, Satoshi,Okada, Takahiro,Tsurue, Norihiko,Okuda, Kensuke,Nagasawa, Hideko
supporting information, p. 4156 - 4162 (2014/04/17)
An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study. In the same pot: [1,2,3]Triazolo[1,5-a] pyridines are synthesized from the corresponding 2-acylpyridines by a one-pot method, consisting of hydrazonation followed by oxidative cyclization through copper(II)-catalyzed N-N bond formation (see scheme).
Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: Isolation and reversible formation of the putative metallacycle intermediate
Park, Boyoung Y.,Montgomery, T. Patrick,Garza, Victoria J.,Krische, Michael J.
supporting information, p. 16320 - 16323 (2013/12/04)
Heteroaromatic secondary alcohols react with isoprene to form products of hydrohydroxyalkylation in the presence of ruthenium(0) catalysts generated from Ru3(CO)12 and tricyclohexylphosphine, enabling direct conversion of secondary to tertiary alcohols in the absence of premetalated reagents or stoichiometric byproducts. The putative oxaruthenacycle intermediate has been isolated and characterized, and reversible metallacycle formation has been demonstrated.
Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides
Li, Zhou,Gevorgyan, Vladimir
supporting information; experimental part, p. 2808 - 2810 (2011/05/05)
An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br + and CN- to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one-pot access to densely substituted cyanoepoxides from easily available ketones (see scheme). Copyright
