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
Chemo/regioselective Aza-Michael additions of amines to conjugate alkenes catalyzed by polystyrene-supported AlCl3
Dai, Liyan,Zhang, Yi,Dou, Qianqian,Wang, Xiaozhong,Chen, Yingqi
, p. 1712 - 1716 (2013/03/13)
A simple and efficient procedure is presented for Aza-Michael additions of various amines with conjugate alkenes bearing electron withdrawing group catalyzed by polystyrene-supported aluminum chloride (Ps-AlCl3) without the use of any solvents. The catalyst shows high catalytic activity for both aromatic amines and aliphatic amines. Chemoselective additions of the two types of amines with conjugate alkenes are achieved. Regioselective additions of two different amino groups in one molecule proceed smoothly. Ps-AlCl 3 has better recyclability and can be reused several times without apparent loss of activity.
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.
LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions
Azizi, Najmedin,Saidi, Mohammad R.
, p. 383 - 387 (2007/10/03)
Several primary and secondary amines were added to α,β- unsaturated esters, nitriles, amides, and ketones to give the corresponding saturated amines mediated by solid lithium perchlorate under solvent-free and environmentally friendly conditions at room temperature.
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.
