-SDS- System: A highly Efficient Dual Catalytic Green System for Deprotection of Imines and in Situ Preparation of Bis(indolyl)alkanes from Indoles in Water
A novel catalytic system consisting of I2-SDS-H2O has been developed which cleaves 2,3-diaza-1,3-butadiene, 1-aza-1,3-butadienes, oximes and in presence of indoles in the medium uses the corresponding aldehyde products to produce bis(indolyl)alkanes in situ. This one pot simple and mild dual catalytic system works in water at room temperature under neutral conditions. 1. Introduction Using water as solvent in the organic reactions is one of the most important targets to organic chemists because of the easy availability, nontoxicity, and ecofriendly nature of the water [1–7]. In this endeavour, a number of chemical reactions such as Diels Alder, hetero Diels-Alder, 1,3-dipolar cycloaddition, oxidations, reductions, and others are performed successfully in water [1–3]. Also, it is reported that in few cases addition of the water increases the rate and the yield of a reaction and also enhances the enantioselectivity in a chiral synthesis [8]. But the main problems associated with water as a solvent is its poor ability to solubilise organic reactants and incapability to create anhydrous condition for moisture sensitive organic compounds and catalysts. To overcome the solubility problem, generally a surfactant is introduced to the reaction mixture. The surfactant, due to its hydrophobic and hydrophilic nature, forms micelles with water insoluble organic compounds and promote the desired reactions to occur inside the hydrophobic ambience of the micelle core [9, 10]. Cleavage of the C=N bonds is a very important transformation in organic synthesis as the C=N functionality is widely used to protect both the carbonyl and amines. There are a number of methods used for the cleavage of C=N bonds which include acidic reagents [11–13], oxidizing agents [14], metallic salts [15, 16], (PhSeO)2O [17], NaHSO3 [18], and others. Most of these methodologies suffer from serious drawbacks like involvement of strong Lewis and Bronsted acids, use of toxic and costly transition metals (i.e., Cr, Pd, Co), low temperature, longer reaction time, low yield, and difficulties in isolating the products. Therefore, development of efficient, mild and environment friendly reagents are always necessary. On the other hand, bisindoles are recently emerging as extremely important class of compounds because of their novel antibacterial and anticancer activities [19–21]. That is why a number of methodologies have also been postulated for the synthesis of bisindoles [22–29]. In our previous communications, we reported that surfactant- (SDS-) mediated cleavage of C=N bonds could be achieved with
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