- One-pot reductive amination of acetals with aromatic amines using decaborane (B10H14) in methanol
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Aldehyde acetals and ketone ketals were reductively aminated in one pot with aromatic amines to give the corresponding amines in methanol or aqueous methanol in good to high yields. This direct method might be important because acetals and ketals are used as a popular protecting group for aldehyde and ketones. The advantage of our method is effective even in an aqueous solution and in the application to selective reaction.
- Park, Eun Soo,Lee, Ji Hee,Kim, Soo Jung,Yoon, Cheol Min
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- GPhos Ligand Enables Production of Chiral N-Arylamines in a Telescoped Transaminase-Buchwald-Hartwig Amination Cascade in the Presence of Excess Amine Donor
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The combination of biocatalysis and chemocatalysis can be more powerful than either technique alone. However, combining the two is challenging due to typically very different reaction conditions. Herein, chiral N-aryl amines, key features of many active pharmaceutical ingredients, are accessed in excellent enantioselectivity (typically>99.5 % ee) by combining transaminases with the Buchwald-Hartwig amination. By employing a bi-phasic buffer-toluene system as well as the ligand GPhos, the telescoped cascade proceeded with up to 89 % overall conversion in the presence of excess alanine. No coupling to alanine was observed.
- Heckmann, Christian M.,Paradisi, Francesca
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supporting information
p. 16616 - 16620
(2021/10/12)
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- Synthesis, reactivities, and catalytic properties of iodo-bridged polymeric iridium complexes with flexible carbon chain-bridged bis(tetramethylcyclopentadienyl) ligands
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Dinuclear iridium complexes [(C5Me4)(CH 2)n(C5Me4)][Ir(COD)]2 (2a: n = 2; 2b: n = 3; 2c: n = 4) are obtained from the reactions of the corresponding dilithium salts Li2/sub
- Tan, Xing,Li, Bin,Xu, Shansheng,Song, Haibin,Wang, Baiquan
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p. 3253 - 3261
(2013/07/19)
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- Aminohaloborane in Organic Synthesis. IX. Exclusive ortho Acylation Reaction of N-Monoaminoalkylanilines
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The exclusive ortho acylation reaction of aniline derivatives using boron trichloride made possible the one-step synthesis of 2-acyl-N-monoaminoalkylanilines (1) and the corresponding imines (2) from N-monoaminoalkylanilines, even in the case of compounds with a bulky substituent at the nitrogen atom.Conventional methods only give 1 via elaborate procedures.Keywords: regioselective reaction; 2-acylaniline derivative; 2-acylaniline-imine derivative; boron trichloride
- Adachi, Makoto,Sasakura, Kazuyuki,Sugasawa, Tsutomu
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p. 1826 - 1835
(2007/10/02)
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- ALCOHOLS AND ALUMINIUM ALKOXIDES IN THE PRESENCE OF RANEY-NICKEL AS ALKYLATING AGENTS. II. A KINETIC STUDY OF ALKYLATION OF AROMATIC AMINES
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The kinetics of N-alkylation of substituted anilines with isopropanol and aluminium isopropoxide, catalysed by Raney-nickel, have been studied.The reaction proceeds according to a second-order equation.The formation of the Schiff's bases of the anilines along the reaction courses have been detected.The data reported also show that the reaction rates depend upon the nucleophilicity of the substrate to be alkylated.A possible mechanism is discussed.
- Angelis, Francesco De,Ferretti, Gabriella,Botta, Maurizio,Grgurina, Ingeborg,Nicoletti, Rosario
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p. 267 - 272
(2007/10/02)
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