Coordination of Cyclic (Alkyl)(Amino) Carbenes to an Iron Center Through Use of Internal Bases Restricted; Files Only

Abstract

The growth in use of organometallic and inorganic compounds has led to large developments in realms such as catalysis and synthesis. With this growth, pushes toward first-row transition metal chemistry have led to the evolution of corresponding ligands such as cyclic (alkyl)(amino) carbenes (CAACs). Current metalation of these ligands oftentimes proves inefficient, leading to a desire for a streamlined method for ligation. This report discusses the use of the internal bases Fe(TMP)2 (bis(2,2,6,6-tetramethylpiperidide)iron(II)) and Fe(HMDS)2 (bis[bis(trimethylsilyl)amido]iron(II)) to conduct a concurrent deprotonation and ligation of a monodentate CAAC to an iron center, as well as expansions into the size, denticity, and counterion impacts on the CAAC’s reactivity with said internal bases. These findings show that these internal bases function to deprotonate and ligate mid-sized iminium salts with halide counterions onto an iron center, while also displaying unprecedented reactivity to be further researched.

Table of Contents

1. Introduction.........................9

2. Results and Discussion..........12

2.1 Diisopropylamine CAAC.......12

2.2 Hemilabile CAAC.................18

2.3 Isopropyl Arm CAAC............22

3. Conclusion and Future Steps...23

4. Experimental Section..............25

5. References..............................35

About this Honors Thesis

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School	Emory College
Department	Chemistry
Degree	B.S.
Submission	Honors Thesis
Language	English
Research Field	Chemistry, Inorganic
Palavra-chave	iron ligand cyclic (alkyl)(amino) carbene organometallic
Committee Chair / Thesis Advisor	Feng Zhai, Emory University
Committee Members	Richard Himes, Emory University Matthew Weinschenk, Emory University

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