I2-SDS-H2O System: A highly Efficient Dual Catalytic Green System for Deprotection of Imines and in Situ Preparation of Bis(indolyl)alkanes from Indoles in Water

Parasa Hazarika,Pallab Pahari,Dilip Konwar,Manash Jyoti Borah

doi:10.5402/2012/635835

Parasa Hazarika, Pallab Pahari + Show 2 more

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https://doi.org/10.5402/2012/635835

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Abstract

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.

Highlights

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 [1,2,3,4,5,6,7]
We reported that surfactant- (SDS-) mediated cleavage of C=N bonds could be achieved with acetic anhydride [30] and surfactant-I2water can be used for the deprotection of imines to carbonyls [31]
We have shown that bis- and trisalkanes can be synthesized in presence of Bronsted acid in water [32]

Summary

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 [1,2,3,4,5,6,7]. There are a number of methods used for the cleavage of C=N bonds which include acidic reagents [11,12,13], 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. [33] for the cleavage of 2,3-diaza-1,3-butadiene, 1-aza-1,3butadienes, and oximes to produce carbonyls and amines, and the resulting reaction mixture reacts with indoles to produce bis (indolyl)alkanes in situ at room temperature under neutral conditions

Results and Discussion

Entry a Indoles 2 b c d e f g h

Conclusions

Experimental