112971-19-4Relevant articles and documents
Chemoselective catalytic conjugate addition of alcohols over amines
Uesugi, Shuhei,Li, Zhao,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 1611 - 1615 (2014/03/21)
A highly chemoselective conjugate addition of alcohols in the presence of amines is described. The cooperative nature of the catalyst enabled chemoselective activation of alcohols over amines, allowing the conjugate addition to soft Lewis basic α,β-unsaturated nitriles. Divergent transformation of the nitrile functionality highlights the utility of the present catalysis. The cooperative nature of a copper catalyst enabled the highly chemoselective activation of alcohols in the presence of amines and thus the conjugate addition of the hydroxy group to soft Lewis basic α,β-unsaturated nitriles. The presented method proceeds under proton-transfer conditions, reverses the innate reactivity of the OH and NH groups, and does not require protecting groups. dppe=1,2-bis(diphenylphosphino) ethane, MeSal=3-methylsalicylate. Copyright
RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang
, p. 2129 - 2136 (2007/10/03)
The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl 3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls. Georg Thieme Verlag Stuttgart.
Indium trichloride-catalyzed conjugate addition of amines to α,β-ethylenic compounds in water
Loh, Teck-Peng,Wei, Lin-Li
, p. 975 - 976 (2007/10/03)
Catalytic amount of indium (III) trichloride efficiently catalyzed Michael reaction between amines and α,β-ethylenic compounds in water and under mild conditions. Indium trichloride can be recovered and reused without decrease in yield.