Development and Applications of Electron-Transfer-Initiated Cyclization Reactions

Abstract

This account describes the work done by my group on electron-transfer-initiated cyclization reactions. In this work radical-cation formation initiates bond cleavage processes that form electrophilic groups leading to reactions with pendent nucleophiles to form cyclic structures. The discussion begins with an overview of the relevant concepts that inspired the work and opportunities that single-electron oxidation provides. Our early work in which we optimized the procedure, elucidated the mechanism, and determined the scope of the process will be discussed in detail, followed by applications that were devised based on these studies.

• 1 Introduction

• 2 Reaction Optimization and Mechanistic Studies

• 3 Applications to Heterocycle Synthesis through Carbon-Heteroatom Bond Formation

• 4 Development of Carbon-Carbon Bond-Forming Processes

• 5 Summary and Future Prospects

Key words

electron transfer - cyclization - cleavage - heterocycles - oxidation

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This possibility was graciously suggested by an anonymous referee.