Abstract: Transition metal catalyzed direct functionalization of C-H bonds have brought a paradigm shift in organic chemistry. Instead of long sequence of reactions to incorporate a new functionality, this process relies on selective functionalization of otherwise unreactive C-H bonds and thus brings about the desired transformation in a step and atom economical fashion.
During the early days of development of this field, second and third row transition metals such as Iridium (Ir), Rhodium (Rh), Ruthenium (Ru) and Palladium (Pd) were employed. They were robust and efficient however the major disadvantages of these metals were their high cost, high toxicity and sensitivity towards air and moisture degradation. To circumvent these disadvantages, the first row transition metals such as Manganese (Mn), Cobalt (Co), Nickel (Ni), Copper (Cu) etc. has emerged as potential alternatives.
In my doctoral research I have developed first tow transition metal catalyzed methodologies for functionalization of C-H bonds and applied them towards the synthesis of functionalized bio-active heterocycles and building blocks. In the first chapter of my thesis I have given a brief literature review on first row transition metal catalyzed C-H activation/functionalization to convey the fundamental idea of the field. In the second and third chapter we have demonstrated the synthesis of polyaryl heteroarenes through regioselective C-H activation by utilizing high valent Cp*Co-based catalysts.
In the fourth chapter we have demonstrated our research on developing a novel titanium oxide supported cuprous iodide nano catalyst. The catalyst is extensively characterized and successfully applied C-H amination of azoles. To establish the utility of our strategy further, we have utilized our catalyst for the synthesis of a bio-active molecule which is known to show potential anti HIV and anti-tumor property. In the final chapter of my thesis, we have shown the successful extension of our previously developed methodology with copper nanocatalyst. We have synthesized α-arylketoamide through C(sp)-H functionalization utilizing this titanium supported CuI nano catalyst.
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Ph.D. dissertation, Shiv Nadar University 2019 "Metal catalyzed C-H functionalization: Accessing diverse bio-active heterocycles and building blocks.
List of publications:
Pratip K Dutta, Subhabrata Sen* (Benz)imidazole directed Cobalt (III) catalyzed C-H activation of arenes: A facile strategy to access polyheteroarenes by oxidative annulation. European Journal of Organic Chemistry, 2018, 40, 5512-5519.
Pratip K Dutta, Mahesh Ravva, Subhabrata Sen* Cobalt catalyzed, hydroxyl assisted C-H functionalization: Access to diversely substituted polycyclic pyrans.Journal of Organic Chemistry, 2019, 84, 1176-1184.
Pratip K Dutta, Subhabrata Sen*, Debasree Saha*, Basab Bijoyi Dhar Solid supported Nano structured Cu-catalyst for solvent and ligand free C2 amination of azoles. European Journal of Organic Chemistry, 2018, 657–665.
Pratip K Dutta, Basab Bijayi Dhar, Subhabrata Sen* Aerobic oxidative amidation of alkynes using titanium oxide encapsulated cuprous iodide nanoparticles (CuI@TiO2). new Journal of Chemistry, 2018, 42, 12062--12071.
Research Advisor: Dr. Subhabrata Sen