Selenenate Anions (PhSeO−) as Organocatalyst: Synthesis of trans‐Stilbenes and a PPV Derivative

Abstract

AbstractThe selenenate anion (RSeO−) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans‐stilbenes. It is shown that RSeO− is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO−) and selenolate anions (RSe−) in the aforementioned reaction. This catalytic system was also applied to the benzylic‐chloromethyl‐coupling polymerization (BCCP) of a bis‐chloromethyl arene to form ppv (poly(p‐phenylene vinylene))‐type polymers with high yields, Mn (average molecular weight) up to 13,000 and Đ (dispersity) of 1.15.magnified image