1.6 Sulfur-, Selenium-, and Silicon-Centered Radicals

Abstract

Sulfur-, selenium-, and silicon-centered radicals are versatile reaction intermediates in modern synthetic organic chemistry. These radicals are capable of adding to carbon–carbon multiple bonds such as alkene and arenes, thus introducing the corresponding elements into the products. These radicals can also serve as mediators of free-radical reactions, including as polarity-reversal catalysts, asymmetric catalysts, and halogen-atom abstraction agents, without these elements being incorporated into the products of the reactions. This chapter describes the utility of sulfur-, selenium-, and silicon-centered radicals in two sections. The first covers reactions involving incorporation of the corresponding elements into the products, while the second describes reactions using these radicals as catalysts or reagents to prepare products that do not contain the corresponding elements.

Key words

radicals - sulfur - selenium - silicon - radical addition - arylation - hydrogen-atom abstraction - halogen-atom abstraction - polarity-reversal catalysis - asymmetric catalysis - photoredox catalysis

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