345252-17-7Relevant academic research and scientific papers
Iridium-Catalyzed Reductive Alkylations of Secondary Amides
Ou, Wei,Han, Feng,Hu, Xiu-Ning,Chen, Hang,Huang, Pei-Qiang
supporting information, p. 11354 - 11358 (2018/08/28)
Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.
Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes
Tien, Chieh-Hung,Adams, Matt R.,Ferguson, Michael J.,Johnson, Erin R.,Speed, Alexander W. H.
, p. 5565 - 5568 (2017/10/25)
The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.
Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes
Adams, Matt R.,Tien, Chieh-Hung,McDonald, Robert,Speed, Alexander W. H.
, p. 16660 - 16663 (2017/12/13)
The first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three-step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %) catalyst loadings. Twenty examples of asymmetric reduction employing this main-group catalysis protocol, including the synthesis of the pharmaceuticals ent-rasagiline and fendiline, are shown.
Axial stereocontrol in: Tropos dibenz [c, e] azepines: The individual and cooperative effects of alkyl substituents
Balgobin, Sinead M. C.,Brookes, Dominic J.,Jiang, Junxiang,Pritchard, Robin G.,Wallace, Timothy W.
, p. 10184 - 10199 (2017/12/26)
6,7-Dihydro-5H-dibenz[c,e]azepines, a class of secondary amine incorporating a centre-axis chirality relay, can be prepared from N-(2-bromobenzyl)-N-(1-arylalkyl)methanesulfonamides via Pd-catalysed intramolecular direct arylation, and methylated at C(7)
Palladium-catalyzed aza-wittig-type condensation of isoxazol-5(4H)-ones with aldehydes
Okamoto, Kazuhiro,Shimbayashi, Takuya,Tamura, Eisuke,Ohe, Kouichi
, p. 1490 - 1494 (2014/03/21)
This paper describes the development of a palladium-catalyzed decarboxylative inter- and intramolecular condensation reaction of isoxazol-5(4 H)-ones with carbonyl compounds in the presence of PPh3, giving various 2-azabuta-1,3-dienes or pyrrol
Electrochemical allylation reactions of simple imines in aqueous solution mediated by nanoscale zinc architectures
Huang, Jing-Mei,Wang, Xu-Xiao,Dong, Yi
experimental part, p. 924 - 927 (2011/03/20)
I zinc we're alone now: The title reactions were achieved in an undivided cell fitted with a pair of zinc electrodes in aqueous solution. A preliminary study on the relationship of reaction activity and surface morphology showed that the deposited zinc powders with nanoscale architectures had very high activity.
Indium (Zinc)-copper-mediated barbier-type alkylation reaction of nitrones in water: Synthesis of amines and hydroxylamines
Yang, Yong-Sheng,Shen, Zhi-Liang,Loh, Teck-Peng
supporting information; experimental part, p. 1209 - 1212 (2009/08/07)
An efficient method for the Barbier-type alkylation reaction of various nitrones (including chiral version) and alkyl halides in water is described. The amines and hydroxylamines can be obtained in good yields, depending on the judicious choice of the metal complexes used.
Indium-silver- and zinc-silver-mediated barbier-grignard-type alkylation reactions of imines by using unactivated alkyl halides in aqueous media
Shen, Zhi-Liang,Cheong, Hao-Lun,Loh, Teck-Peng
experimental part, p. 1875 - 1880 (2009/04/06)
In the presence of In or Zn/AgI/InCl3, an efficient and practical method for the Barbier-Grignard-type alkylation reactions of simple imines by using a one-pot condensation of various aldehydes, amines (including the aliphatic and chiral version), and secondary alkyl iodides has been developed. The reaction proceeded more efficiently in water than in organic solvents. Without the use of CuI, it mainly gave the imine self-reductive coupling product, which was not the alkylated product. Good diastereoselectivities (up to 92:8 dr) were obtained when L-valine methyl ester was used as the substrate.
Indium - Copper-mediated barbier - Grignard-type alkylation reaction of imines in aqueous media
Shen, Zhi-Liang,Loh, Teck-Peng
, p. 5413 - 5416 (2008/09/17)
An efficient system of In/Cul/InCl3 was developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or
