203577-52-0Relevant academic research and scientific papers
Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air
Nekvinda, Jan,Santos, Webster L.,Snead, Russell F.
supporting information, p. 14925 - 14931 (2021/09/04)
A method has been developed for the facile Cu(ii)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions. The reaction occurs site selectively, favoring internal alkene protoboration to afford 1,1-disubstituted vinylboronic acid derivatives (up to 93?:?7) with modest to good yields. The method has been applied to a variety of phenylallene derivatives as well as alkyl-substituted allenes. This journal is
Palladium-Catalyzed Carbonylative Four-Component Synthesis of β-Perfluoroalkyl Amides
Geng, Hui-Qing,Wu, Xiao-Feng,Zhang, Youcan
supporting information, p. 17682 - 17687 (2021/10/25)
Transition-metal-catalyzed multicomponent carbonylation is one of the most efficient strategies to construct carbonyl-containing compounds. Herein, a palladium-catalyzed four-component perfluoroalkylation/aminocarbonylation of unactivated alkenes with per
Copper-Catalyzed Propargylic Reduction with Diisobutylaluminum Hydride
Kim, Yuna,Lee, Hanseul,Park, Sunga,Lee, Yunmi
supporting information, p. 5478 - 5481 (2018/09/13)
A mild and efficient method for the synthesis of allenes through selective copper-catalyzed hydride addition to propargylic chlorides using commercially available diisobutylaluminum hydride has been developed. This transformation, which is promoted by a readily accessible N-heterocyclic carbene-copper complex, provides a wide range of new and versatile functionalized allenes in good to excellent yields with high regio- A nd stereoselectivities.
Soft propargylic deprotonation: Designed ligand enables au-catalyzed isomerization of alkynes to 1,3-Dienes
Wang, Zhixun,Wang, Yanzhao,Zhang, Liming
supporting information, p. 8887 - 8890 (2014/07/08)
By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned "push" and "pull" forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pKa units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.
Total synthesis of debromoflustramines B and e based on the intramolecular carbamoylketene-alkene [2 + 2] cycloaddition
Ozawa, Tsukasa,Kanematsu, Makoto,Yokoe, Hiromasa,Yoshida, Masahiro,Shishido, Kozo
supporting information, p. 9240 - 9249,10 (2012/12/12)
Total synthesis of debromoflustramines B and E has been accomplished by using a platinum-catalyzed addition reaction of o-aminophenylboronic acid with the allene and an intramolecular carbamoylketene-alkene [2 + 2] cycloaddition for the construction of the basic carbon framework of the target alkaloids as the key steps.
Total synthesis of debromoflustramines B and e based on the intramolecular carbamoylketene-alkene [2 + 2] cycloaddition
Ozawa, Tsukasa,Kanematsu, Makoto,Yokoe, Hiromasa,Yoshida, Masahiro,Shishido, Kozo
supporting information, p. 9240 - 9249 (2013/01/15)
Total synthesis of debromoflustramines B and E has been accomplished by using a platinum-catalyzed addition reaction of o-aminophenylboronic acid with the allene and an intramolecular carbamoylketene-alkene [2 + 2] cycloaddition for the construction of the basic carbon framework of the target alkaloids as the key steps.
Gold-catalyzed regioselective oxidation ofterminal allenes: Formation of α-methanesulfonyloxy methyl ketones
Luo, Yingdong,Zhang, Guozhu,Hwang, Erik S.,Wilcoxon, Thomas A.,Zhang, Liming
supporting information; experimental part, p. 596 - 600 (2011/06/26)
Synthetically useful α-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-ox
Regiocontrolled addition of arylboronic acids to allenes using palladium and platinum catalysts
Yoshida, Masahiro,Matsuda, Kennosuke,Shoji, Yasunobu,Gotou, Takahiro,Ihara, Masataka,Shishido, Kozo
supporting information; experimental part, p. 5183 - 5186 (2009/06/06)
(Chemical Equation Presented) Studies about the regiocontrolled addition of arylboronic acids to allenes using a palladium or a platinum catalyst have been described. The selectivity of the reaction can be altered by the choice of the metal reagent and base. Contrary to the formation of endo-olefinic products in the reactions using hydroxopalladium complex, predominant production of exo-olefinic products was observed by the reaction with hydroxoplatinum complex.
