2.11 Radical–Radical Cross-Coupling Reactions

Abstract

Due to nearly diffusion-limited radical–radical coupling, synthetically useful, selective radical–radical cross-coupling reactions remain challenging. However, different radical lifetimes and various radical initiation approaches now provide the possibility for radical–radical cross-coupling. In this chapter, recent advances in radical–radical cross-coupling reactions are described. In the first part, a basic kinetic phenomenon called the persistent radical effect is briefly reviewed and explained. The remainder of the chapter presents a series of case studies, illustrating several types of radical–radical cross couplings in a variety of disparate settings.

Key words

radical–radical cross coupling (RRCC) - persistent radicals - transient radicals - persistent radical effect - single-electron transfer - C—C bond formation - metal-free coupling - radical–metal crossover

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• 156 Acknowledgement: Financial support was provided by the Robert A. Welch Foundation (Grant I-2010–20 190 330) and the Eugene McDermott Scholar Endowed Scholarship. We thank Drs. Ming Yan, Rohan R. Merchant, and Jacob T. Edwards for helpful discussions and proofread during manuscript preparation.