82940-37-2Relevant academic research and scientific papers
Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles
Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
, p. 7094 - 7098 (2021/04/16)
A reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant is reported. This protocol represents an unprecedented approach to the chemoselective synthesis of α-hydroxy ketones by electrophile–electrophile cross-coupling.
Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines
Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, (2020/02/04)
A copper-catalyzed enantioselective reductive cross-coupling using aromatic aldehydes and imines, producing chiral β-amino alcohols, is described. The catalytic formation of enantioenriched chiral α-alkoxyalkylcopper(I) species from aromatic aldehydes and the subsequent reaction with imine electrophiles are attractive features of this protocol.
Reductive coupling between aromatic aldehydes and ketones or imines by copper catalysis
Takeda, Mitsutaka,Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3664 - 3669 (2019/02/14)
The copper-catalyzed reductive coupling of two different carbonyl compounds has been achieved. The reaction of aromatic aldehydes and arylketones with a silylboronate in the presence of a catalytic amount of a CuCl-N-heterocyclic carbene (NHC) complex and a stoichiometric amount of alkoxide base yielded cross-coupled 1,2-diol derivatives. A reaction pathway is proposed that involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species from the aromatic aldehyde and its subsequent coupling with the arylketone. This process was amenable to asymmetric catalysis. This copper catalyst system also enabled the reductive coupling between aromatic aldehydes and imines.
Mesoporous Titania-Iron(III) Oxide with Nanoscale Porosity and High Catalytic Activity for the Synthesis of β-Amino Alcohols and Benzimidazole Derivatives
Roy, Susmita,Banerjee, Biplab,Salam, Noor,Bhaumik, Asim,Islam, Sk. Manirul
, p. 2689 - 2697 (2015/09/15)
A mesoporous TiO2-Fe2O3 mixed oxide material (MTF-1E) with nanoscale porosity and a high BET surface area was synthesized using sodium dodecyl sulfate (SDS) as a structure-directing agent. The material was characterized by
Fe(OH)3 nano solid material: An efficient catalyst for regioselective ring opening of aryloxy epoxide with amines under solvent free condition
Shah, Arpan K.,Prathap, K. Jeya,Kumar, Manish,Abdi, Sayed H.R.,Kureshy, Rukhsana I.,Khan, Noor-ul H.,Bajaj, Hari C.
, p. 442 - 450 (2017/02/05)
Iron hydroxide-Fe(OH)3and iron oxides (Fe3O4and Fe2O3) were successfully prepared and characterized. These materials were employed as efficient and environmentally benign heterogeneous catalysts for t
Enantioselective ring-opening of meso-epoxides by aromatic amines catalyzed by a homochiral metal-organic framework
Regati, Sridhar,He, Yabing,Thimmaiah, Muralidhara,Li, Peng,Xiang, Shengchang,Chen, Banglin,Zhao, John Cong-Gui
, p. 9836 - 9838 (2013/10/21)
The enantioselective ring-opening of meso-epoxides by aromatic amines was achieved by using a new chiral metal-organic framework UTSA-32a. The corresponding α-hydroxyamines were obtained with good yields and ee values (up to 89% ee).
Asymmetric ring opening of meso-epoxides with aromatic amines using (R)-(+)-BINOL-Sc(OTf)3-NMM complex as an efficient catalyst
More, Ganesh V.,Bhanage, Bhalchandra M.
, p. 6900 - 6906 (2013/11/06)
This work reports the asymmetric ring-opening reaction of meso-epoxides with aromatic amines by using the highly efficient in situ generated (R)-(+)-BINOL-Sc(OTf)3-N-methylmorpholine complex. The asymmetric ring opening of cis-stilbene oxide wi
Titanium-mediated cross-coupling reactions of imines with ketones or aldehydes: An efficient route for the synthesis of 1,2-amino alcohols
Fan, Guoqin,Liu, Yuanhong
supporting information; experimental part, p. 5084 - 5087 (2012/09/25)
The cross-coupling reactions of imines with ketones using Ti(O iPr)4/c-C5H9MgCl reagent lead to 1,2-amino alcohols after hydrolysis. The coupling reactions with aldehydes could also afford 1,2-amino alcohols, however, in some cases, aziridines were obtained as major products in a stereoselective manner.
Zinc tetrafluoroborate hydrate as a mild catalyst for epoxide ring opening with amines: Scope and limitations of metal tetrafluoroborates and applications in the synthesis of antihypertensive drugs (RS)/(R)/(S)-metoprolols
Pujala, Brahmam,Rana, Shivani,Chakraborti, Asit K.
scheme or table, p. 8768 - 8780 (2011/12/04)
The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF4) 2?xH2O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF4)2?xH2O ? Cu(BF4)2?xH2O > Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > LiBF4 for reactions with cyclohexene oxide and Zn(BF4)2?xH2O ? Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > Cu(BF4)2?xH2O for stilbene oxide, but AgBF4 was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pKa of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.
Thieme chemistry journal awardees-where are they now? bifunctional organocatalysis with N-Formyl-l-proline: A novel approach to epoxide ring opening and sulfide oxidation
Wei, Shengwei,Stingl, Kerstin A.,Wei?, Katharina M.,Tsogoeva, Svetlana B.
experimental part, p. 707 - 711 (2010/06/13)
A conceptually distinct approach to the aminolysis of 1,2-epoxides, which involves Lewis base-Br?nsted acid catalysis employing N-formyl-l-proline as an easily accessible bifunctional organocatalyst and water as a solvent is presented. The potential of N-formyl-l-proline as organocatalyst for the sulfide oxidation reaction using aqueous hydrogen peroxide as environmentally benign and readily available oxidant is also demonstrated. Good to high yields are achieved for both reactions. Georg Thieme Verlag Stuttgart ? New York.
