Catalytic amide base system generated in situ for 1,3-diene formation from allylbenzenes and carbonyls

Abstract

The amide base generated in situ from tetramethylammonium fluoride and N(TMS)₃ catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role of trans β-methyl stilbenes in product formation is also elucidated.