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Thiyl radicals: from simple radical additions to asymmetric catalysis.

Radicals derived from thiols, often termed as thiyl radicals, are important intermediates in biological processes as well as in synthetic organic chemistry. The ubiquitous nature of such intermediates is mainly due to their ease of formation and inherent reactivity: the S H homolytic bond dissociation energy (BDE) is about 87 kcalmol 1 for alkanethiols, 79 kcal mol 1 for thiophenols, and the S S BDE is about 50– 65 kcal mol 1 for disulfides. Thiyl radicals are capable of abstracting a hydrogen atom from ethers as well as allylic and benzylic systems reversibly. These properties make them unique for the design of new organocatalysts. The ability of thiyl radicals to add to carbon–carbon and carbon–heteroatom multiple bonds makes them one of the powerful intermediates in chemical synthesis. The addition of these radicals to olefins is generally facile and reversible (Table 1). The rate of addition and fragmentation become