Indium Trichloride-Catalyzed Conjugate Addition of Amines to α,β-Ethylenic Compounds in Water

Abstract

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.

Accelerated C–N Bond Formation in Dropcast Thin Films on Ambient Surfaces

“…It represents a valuable synthetic alternative to the established Mannich reaction (Scheme 1b). Under bulk solution-phase conditions, the azaMichael addition is catalyzed by Lewis acids [2,3] (under strictly anhydrous conditions), metal catalysts [4][5][6] [e.g., Yb(OTf) 3 , InCl 3 , FeCl 3 .7H 2 O/CO(OAc) 2 ], oxidizing agents [7,8] (e.g., ceric ammonium nitrate) or N-heterocyclic carbenes [9] generated by treating imidazolium salts with a base). In this study, interfacial versions of the aza-Michael addition and Mannich reactions were carried out under ambient conditions in high yields (on a small scale) without the use of catalyst.…”

Conjugated Addition of Amines to Electron Deficient Alkenes: A Green Approach

“…But usually both these additions are carried out in presence of a strong base or acid [8,9]. Several methods are available in the literature by using different catalysts such as Yb(OTf) 3 [10], CeCl 3 ·7H 2 O-NaI [11], InCl 3 [12], Cu(OTf) 2 [13,14], CAN [15], KF/alumina [16,17], LiClO 4 [18], Bi(OTf) 3 [19], Bi(NO) 3 [20], SmI 2 [21], Cu(acac) 2 /ionic liquid [22], ionic liquid/ quaternary ammonium salt [23,24], boric acid [25], borax [26] [30], MnCl 2 [31]etc. Although these methods have their own advantages and quite useful, but some of these methods used a large excess of reagents, hazardous solvents such as acetonitrile or 1,2-dichloroethane, require long time and harsh reaction.…”

Cu(acac)2 Immobilized in Ionic Liquids: A Recoverable and Reusable Catalytic System for Aza‐Michael Reactions

“…However, these reactions require either basic conditions [7] or acidic catalysts [8] which seem to be detrimental to the desired synthesis. In order to overcome some of the disadvantages, a good number of alternative procedures have been reported over the past few years using Yb(OTf) 3 , [9] InCl 3 , [10] CeCl 3 · 7 H 2 O, [11] Bi(NO) 3 [14] LiClO 4 [15] and heterogeneous solid acids, [16] but the need for an environmentally benign and facile protocol still exists. Room temperature ionic liquids are acknowledged as eco-benevolent alternatives to volatile organic solvents and have also other useful properties like very low vapor pressure, wide liquid range, high thermal stability and possess highly conductive solvation ability for a variety of organic substrates and catalysts including Lewis acids and enzymes.…”