Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and Polycitrin A

Synlett

Volumn , Issue 18, 2006, Pages 3145-3149

  Burtoloso, Antonio Carlos B ^a   Garcia, Ariel L L ^a   Miranda, Karen C ^a   Correia, Carlos Roque D ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

3,4 diarylmaleic anhydrides; Arenediazonium tetrafluoroborates; Fluorescent materials; Heck arylation; Polycitrin A

Indexed keywords

ALKALOID DERIVATIVE; BORIC ACID; MALEIC ANHYDRIDE; POLYCITRIN A; PREPOLYCITRIN A; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; HECK REACTION; SYNTHESIS;

EID: 33751281975     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951524     Document Type: Article

References (23)

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23. 2 in 3 mL of MeCN was added anisole (0.8 mL of a 0.1 M solution in MeCN) and 2,3-dihydrofuran (0.2 mL of a 0.1 M solution in MeCN). After 5 min, 49 mg of maleic anhydride (0.5 mmol), 123 mg of NaOAc (1.5 mmol) and 443 mg of 4-methoxybenzene-diazonium tetrafluoroborate (2 mmol) were added and the reaction mixture refluxed for 1 h. After cooling, the reaction mixture was diluted with 15 mL of EtOAc and filtered through a short pad of Celite®. The solvent was then evaporated in vacuo and the residue flash chromatographed (SiO2, hexane-EtOAc = 8:2) to provide 93 mg (60% yield) of the Heck adduct 3 as homogeneous material by TLC.