53053-99-9Relevant articles and documents
Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines
Higuchi, Takafumi,Tagawa, Risa,Iimuro, Atsuhiro,Akiyama, Shoko,Nagae, Haruki,Mashima, Kazushi
, p. 12795 - 12804 (2017/09/06)
Selective dehydrogenative synthesis of imines from a variety of alcohols and amines was developed by using the ruthenium complex [RuCl2(dppea)2] (6 a: dppea=2-diphenylphosphino-ethylamine) in the presence of catalytic amounts of Zn(OCOCF3)2 and KOtBu, whereas the selective dehydrogenative formation of amides from the same sources was achieved by using another ruthenium complex, [RuCl2{(S)-dppmp}2] [6 d: (S)-dppmp=(S)-2-((diphenylphosphenyl)methyl)pyrrolidine], in the presence of catalytic amounts of Zn(OCOCF3)2 and potassium bis(trimethylsilyl)amide (KHMDS). Our previously reported ruthenium complex, [Ru(OCOCF3)2(dppea)2] (8 a), was the catalyst precursor for the imine synthesis, whereas [Ru(OCOCF3)2{(S)-dppmp}2] (8 d), which was derived from the treatment of 6 d with Zn(OCOCF3)2 and characterized by single-crystal X-ray analysis, was the pre-catalyst for the amide formation. Control experiments revealed that the zinc salt functioned as a reagent for replacing chloride anions with trifluoroacetate anions. Plausible mechanisms for both selective dehydrogenative coupling reactions are proposed based on a time-course study, Hammett plot, and deuterium-labeling experiments.
Ionic liquid effects on a multistep process. Increased product formation due to enhancement of all steps
Keaveney, Sinead T.,Haines, Ronald S.,Harper, Jason B.
, p. 8925 - 8936 (2015/08/24)
The reaction of a series of substituted benzaldehydes with hexylamine was examined in acetonitrile and an ionic liquid. In acetonitrile, as the electron withdrawing nature of the substituent increases, the overall addition-elimination process becomes fast
A biologically inspired CuI/topaquinone-like co-catalytic system for the highly atom-economical aerobic oxidation of primary amines to imines
Largeron, Martine,Fleury, Maurice-Bernard
scheme or table, p. 5409 - 5412 (2012/06/18)
Acting together: Low catalytic amounts of CuI and topaquinone-like catalyst 1ox (see scheme) are sufficient to activate the α-C-H bond of primary amines, which are converted into alkylated imines under ambient conditions. This atom-economical process tolerates the presence of various reactive functional groups and allows selective cross-coupling of two amines. Copyright