Nano-copper catalysed highly regioselective synthesis of 2,4-disubstituted pyrroles from terminal alkynes and isocyanides

Abstract

Nano-copper(0) stabilized on alumina prepared from Cu-Al hydrotalcite has been reported for completely regioselective synthesis of 2,4-disubstituted pyrroles from unactivated terminal aromatic/aliphatic alkynes and isocyanides. The reaction is operationally simple, involves ligand-free inexpensive nano-copper, and affords products in high yields.

Magnetically Recoverable Cu0/Fe3O4‐Catalysed One‐Pot Tandem Synthesis of Sulfur‐Containing Triazoles from Alkynes and Azide: DMSO Acts as an Alkylating Agent

“…Furthermore, their unique paramagnetic nature and inherent insolubility in most reaction solvents allows them to be simply and efficiently separated from reaction mixtures using an external magnet, in an economical, practical, and environmentally benign way . Recently, our group have prepared Cu 0 /Al 2 O 3 and magnetically separable Cu 0 /Fe 3 O 4 nanocatalysts, and successfully demonstrated their catalytic activities in alkyne–isocyanide cycloaddition reactions to give synthetically challenging 2,4‐disubstitiuted pyrroles and 2,3,4 trisubstitiuted pyrroles, respectively , . In a continuation of this research programme, we report in this paper our new findings on the synthesis of sulfur‐containing triazoles from terminal alkynes and azide in the presence of a magnetically separable and reusable nano Cu 0 /Fe 3 O 4 catalyst (Figure ).…”

Recent Advances in the Chemistry of Isocyanides with Activated Methylene Group

“…Group of Prof. Pravin R. Likhar [ 32 ] discovered that highly efficient regioselective [3+2] cycloaddition of aromatic alkynes 55 with isocyanides 1 is achieved by heterogeneous copper nanoparticles stabilized on alumina. The yield of regioselective 2,4‐disubstituted pyrroles is optimized by the use of appropriate base and solvent without using external ligands.…”

A catalytic synthesis of dihydrofuran‐3(2H)‐imine skeletons from isocyanides, terminal alkynes, and oxiranes

“…In this regard, Huang has developed an important multicomponent reaction using arynes and isocyanides in the presence of terminal alkynes as second nucleophile partner . The cycloaddition of acceptor‐substituted methyl isocyanides with electron‐deficient alkynes has been well documented, previously …”