4198-96-3Relevant academic research and scientific papers
Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
Meng, Shan-Shui,Tang, Xiaowen,Luo, Xiang,Wu, Ruibo,Zhao, Jun-Ling,Chan, Albert S. C.
, p. 8397 - 8403 (2019/09/03)
An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected arylamines using alcohols catalyzed by B(C6F5)3 has been developed. The reaction gives N-alkylated products and ortho C-alkylated products in different solvents in good chemoselectivities and yields. Control experiments and DFT calculations indicated that the borane underwent alcohol/arylamine exchange to ensure catalytic activity, and a possible mechanism involving a carbocation is proposed.
The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
Zhang, Xin,Dai, Yijing,Wulff, William D.
, p. 2015 - 2018 (2018/09/18)
An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
Method for catalyzing benzyl alcohol compound to be aminated
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Paragraph 0040; 0041; 0042, (2019/01/14)
The invention belongs to the field of organic synthesis, and discloses a method for catalyzing a benzyl alcohol compound to be aminated. The method comprises the steps that the benzyl alcohol compoundand an aniline compound are mixed, a solvent and a cata
Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy
Buxton, Craig S.,Blakemore, David C.,Bower, John F.
supporting information, p. 13824 - 13828 (2017/10/24)
Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C?C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C?C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.
Catalytic asymmetric α-iminol rearrangement: New chiral platforms
Zhang, Xin,Staples, Richard J.,Rheingold, Arnold L,Wulff, William D.
, p. 13971 - 13974 (2014/12/10)
A series of 19 different asymmetric catalysts were screened in an effort to identify the first chiral catalyst for the rearrangement of α-hydroxy imines to α-amino ketones involving a 1,2-carbon shift. Although aluminate complexes of VAPOL, VANOL, and 7,7'-tBu2VANOL were quite effective catalysts giving up to 88% ee, the ne plus ultra catalyst for this reaction was found to be a zirconium complex of VANOL which gives 97 to >99% ee for the majority of the substrates examined. An X-ray diffraction study of the catalyst reveals that the zirconium exists as a homoleptic complex with three VANOL ligands and two protonated N-methyl imidazoles.
Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones
Wei, Ye,Deb, Indubhusan,Yoshikai, Naohiko
supporting information; experimental part, p. 9098 - 9101 (2012/07/14)
We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.
Synthesis and characterization of 9,10-bis(arylimino)-9,10-dihydrophenanthrenes, the structure of (Z,Z)-9,10-bis(phenylimino)-9,10-dihydrophenanthrene and PdCl2-[(E,E)-9,10-bis(phenylimino)-9,10-dihydrophenanthrene] in the solid state and in so
Van Belzen, Ruud,Klein, Rene A.,Smeets, Wilberth J.J.,Spek, Anthony L.,Benedix, Roland,Elsevier, Cornelis J.
, p. 275 - 285 (2007/10/03)
The synthesis and characterization of substituted phenanthrene-9,10-quinone diimines of the type 9,10-bis(arylimino)-9,10-dihydrophenanthrene (aryl-BIP) is described. These rigid bisnitrogen ligands have been synthesized by a metal-mediated cyclodehydroge
Stereochemistry of Imino-group Reduction. Part 3. The Hydride Reduction of Achiral Benzil Monoimines
Alcaide, Benito,Lopez-Mardomingo, Carmen,Perez-Ossorio, Rafael,Plumet, Joaquin
, p. 1649 - 1654 (2007/10/02)
The RR,SS:RS,SR ratio of diastereoisomeric amino-alcohols obtained from the lithium aluminium hydride reduction of the monoimines prepared by reaction of benzil and various aliphatic and aromatic achiral amines has been determined.Stereochemical results a
