Reductive debromination of 1,2-dibromides with anisidines

Abstract

vic -Dibromides containing the α-bromocarbonyl or α-bromoaromatic moieties were reductively debrominated to furnish alkenes in high yield. o- and m-Anisidines but not p-anisidine were found to be effective debrominating agents. The reductive debrominations were found to be trans-stereospecific.

cis-β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence

“…20–21 Recently, during our attempt to prepare a vicinal dibromide from cinnamic acid, we isolated a stable β-lactone instead.…”

Competitive, substrate-dependent reductive debromination/dehydrobromination of 1,2-dibromides with triethylamine

“…1 We postulated that these easily oxidizable aromatic compounds affect the elimination via electron transfer to the dibromide, with concomitant double bond formation in a concerted fashion (Scheme 1). …”