Photocatalytic Reaction of Aryl Halides with Tin(II) Acetate to Generate Arylstannane(IV) Reagents
Artem A. Zemtsov, Vyacheslav I. Supranovich, Vitalij V. Levin, Alexander D. Dilman
Abstract
Aromatic organotin(IV) compounds are a valuable class of reagents widely used in cross-coupling reactions. However, the toxicity of the most popular tributyl-substituted arylstannanes, combined with complicated methods for their synthesis, imposes serious limitations. Herein, we report an approach to accessing aryl organotin(IV) reagents directly from aryl halides and cheap inorganic tin(II) acetate. The insertion of tin(II) into the carbon–halogen bond is performed under photocatalytic conditions and proceeds through the generation of aryl radicals. The resulting organotin reagents may be directly employed in Migita–Kosugi–Stille cross-coupling or can be converted into conventional tributyltin compounds by treatment with butylzinc bromide.