Copper Catalyzed C-C, C-N and C-S Bond Formations and Synthesis of Chiral 1,2-Diamine Based Main Chain Polymers
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2009
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The thesis contains five chapters. The first two chapters describe the N-arylation of amides and imidazoles and S-arylation of thiols using Cu2O nanoparticles as a recyclable catalytic system. The third and fourth chapters focus on the synthesis, structure and application of copper complexes for nitroalodol reaction in asymmetric and non-asymmetric versions. The fifth chapter is devoted to the synthesis and application of chiral main chain polymers with optically active (1R,2R)-1,2-diamines for the asymmetric synthesis. 1. Copper(I) Oxide Nanoparticles Catalyzed N-Arylation of Amides and Imidazoles Transition metal catalyzed C-N bond formation via cross-coupling reaction of nitrogen nucleophiles with aryl halides affords powerful tool for the synthesis of vital compounds utilized in biological, material and pharmaceutical sciences. This chapter describes a simple and efficient procedure for the one pot synthesis and catalysis of Cu2O nanoparticles in PEG4000 for the C-N cross-coupling reactions of amides and azoles with aryl iodides under ligand-free conditions (Scheme 1). RR'NH + R'' I RR'N 5 mol % Cu2O nano PEG4000, KOH 120 DC, N2, 3-18 h R'' R'' = Br, OMe, Me, NO2 R' = H, aryl R = alkyl, aryl up to 90 % yield Scheme 1 2. Copper(I) Oxide Nanoparticles Catalyzed S-Arylation of Thiols Methods for the formation of C-S bonds are indispensable tools in synthetic chemistry. Their importance stems from the prevalence of C-S bonds in many molecules that are of biological, pharmaceutical and material interest. This chapter focuses on the C-S cross-coupling of aryl halides with thiols using CuI/PEG400 system with KOH at 110 DC (Scheme 2). Under these conditions a variety of substituted thiols and substituted iodobenzenes underwent reaction to afford the C-S cross coupled products in high yields. vi SH X + R'...
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Supervisor: Tharmalingam Punniyamurthy
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CHEMISTRY