Synthesis of α,ω-Diarylbutadienes and -Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis

Abstract

Readily available cinnamic acid derivatives such as ferulic acid couple with beta-bromostyrenes and 1-bromo-4-phenylbutadiene under palladium catalysis accompanied by decarboxylation to produce the corresponding alpha,omega-diarylbutadienes and -hexatrienes, respectively. Some of the products exhibit solid-state fluorescence.

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

“…The ( E , E )-1,4-diarylbuta-1,3-dienes 1–4 were isolated and characterized spectroscopically (see Supporting Information; Figures S1–S8). Although the stereochemistry of dienes 1–4 cannot be directly derived from the 1 H NMR spectra on the basis of the protons of the diene moiety, the analysis of spin systems by means of MestReC NMR software (Mestrelab Research, Santiago de Compostela, Spain) [21] as well as comparison with literature data [35,36,37,38] allowed us to confirm the diene structure.…”

Transition metal-catalyzed decarboxylative cross-coupling reactions

“…Miura et al reported Pd-catalyzed decarboxylative crosscoupling of alkenyl carboxylic acids with vinyl bromides (Scheme 30) [42]. This reaction can be used for the preparation of conjugated dienes.…”

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

“…It is rare to use a pentadienyl electrophile [35], or to have a diene or simple alkene adjacent to the carboxyl group [20,36–39]. Despite the absence of this type of reactivity, the decarboxylative coupling of a pentadienyl dienoate ( 9 ; Scheme 2) was desirable enough for our group’s synthesis of clinprost that we attempted the reaction [40–41].…”