26029-60-7Relevant academic research and scientific papers
Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis
Bujok, Robert,Morawska, Paulina,Pawlowski, Robert,Stanek, Filip,Stodulski, Maciej
supporting information, p. 2103 - 2112 (2020/03/27)
A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.
Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Junor, Glen P.,Romero, Erik A.,Chen, Xi,Jazzar, Rodolphe,Bertrand, Guy
supporting information, p. 2875 - 2878 (2019/02/13)
Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.
Photochemically Promoted Aza-Diels-Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
Arai, Noriyoshi,Ohkuma, Takeshi
, p. 7628 - 7636 (2017/07/26)
Aza-Diels-Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 °C), affording the cycloaddition product in 97% yield.
Aziridine synthesis in the presence of catalytic amounts of pyridiniums or viologens
Xue, Zheng,Mazumdar, Arindam,Hope-Weeks, Louisa J.,Mayer, Michael F.
, p. 4601 - 4603 (2008/09/21)
Pyridinium and viologen species were found to induce an aziridine-forming reaction from various imines and phenyldiazomethane. The reactions were generally high yielding and demonstrated cis-aziridine selectivity.
A general one-pot, three-component mono N-alkylation of amines and amine derivatives in lithium perchlorate/diethyl ether solution
Heydari, Akbar,Tavakol, Hossein,Aslanzadeh, Saied,Azarnia, Jamshid,Ahmadi, Nafiseh
, p. 627 - 633 (2007/10/03)
An efficient, general procedure for reductive monoalkylation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithium perc
Azaheteroalkene metathesis: Reaction of imines with molybdenum(VI) bis(imide) complexes
Cantrell, Gidget K.,Meyer, Tara Y.
, p. 1551 - 1552 (2007/10/03)
Bis(imide) complexes (dme)Cl2Mo(=NR)2 (R = But, C6H3Pri2-2,6) and (ButO)2Mo(=NAr)2 (Ar = C6H3Pri2-2,6
Facile α/β diastereomerism in organocobalt corrinoids. synthesis, characterization, and thermolysis of α-neopentylcobalt corrinoids
Zou, Xiang,Brown, Kenneth L.
, p. 6689 - 6698 (2007/10/02)
Coenzyme B12 analogs α-neopentylcobinamide (α-NpCbi+) and α-neopentylcobalamin (α-NpCbl), where the bulky organic ligand is in the "lower" (α) axial ligand position, have been synthesized by reductive alkylation of cyanoaquocobinamid
A Facile Oxidation of Secondary Amines to Imines by Iodosobenzene or by a Terminal Oxidant and Manganese or Iron Porphyrins and Manganese Salen as the Catalysts
Larsen, Jan,Joergensen, Karl Anker
, p. 1213 - 1217 (2007/10/02)
The oxidation of secondary amines to imines by iodosobenzene or catalysed by either manganese(III) or iron(III) porphyrins, or by a manganese(III) salen complex with iodosobenzene as the oxygen donor has been investigated.Both aromatic and aliphatic amines can be oxidized smoothly to the corresponding imines with iodosobenzene as the oxidant and the elimination of hydrogen takes place towards the least substituted carbon.Manganese(III) and iron(III) porphyrins and manganese(III) salen are found to catalyse the oxidation of secondary amines to imines with iodosobenzene as the terminal oxidant.Those amines that are less reactive when iodosobenzene is the oxidant, can be converted to the imines in higher yields if a catalyst is added, compared with the uncatalysed reaction.By-products such as carbonyls and nitrones are found in some of these reactions.The manganese(III) salen complex is found to be the best catalyst, followed by manganese(III) porphyrin and iron(III) porphyrin.On the basis of Hammett plots, isotopic labelling studies and other experimental investigations the mechanisms for the uncatalysed and catalysed amine-to-imine oxidations are discussed.
Simple and High Yield Synthesis of Aldimines via Palladium Complex-Catalyzed Reduction of Imidoyl Chlorides
Tanaka, Masato,Kobayashi, Toshi-aki
, p. 967 - 969 (2007/10/02)
Imidoyl chlorides 1 were efficiently reduced to aldimines 2 by molecular hydrogen in the presence of triethylamine and a catalytic amount of bispalladium dichloride
