Abstract
Substituted alkenes are basic structural motifs in a large number of organic molecules and their synthesis has received continuous attention from synthetic chemists. One of the most straightforward methods for constructing substituted alkenes is the Mizoroki–Heck reaction. Generally, this transformation is catalyzed by palladium and mainly deals with the synthesis of substituted alkenes from aryl or vinyl electrophiles. In sharp contrast, the Mizoroki–Heck reaction of alkyl electrophiles has long been considered a challenging transformation due to the decreased rates of oxidative addition and subsequent facile β-hydride elimination. To address this limitation in traditional Mizoroki–Heck reactions, radical processes have been introduced to achieve the alkenylation of alkyl electrophiles. This review provides an overview of the recent developments in alkyl-Mizoroki–Heck-type reactions. Particular attention is paid to the intermolecular Mizoroki–Heck-type reaction between alkyl radicals and terminal alkenes. The limitations and advantages of using different catalytic methods are discussed and compared.
