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Decarboxylative Coupling Reaction Of CF3CH2I With (Hetero) Aromatic Carboxylates And Coupling Reaction Of Allylalcohol With 3-Pyridyl Boric Acids

Posted on:2017-01-10Degree:MasterType:Thesis
Country:ChinaCandidate:L WangFull Text:PDF
GTID:2284330485485422Subject:Medicinal chemistry
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In the thesis, a novel trifluoroethylation reaction of CF3CH2 I with(hetero)aromatic carboxylates by decarboxylative coupling reaction and an efficient oxidation coupling reaction of allylalcohol with 3-pyridyl boric acids have been researched.1. Decarboxylative coupling reaction of CF3CH2 I with(hetero)aromatic carboxylatesa) Synthesis of(hetero)aromatic carboxylatesThe corresponding(hetero)aromatic carboxylates was obtained by the reaction of(hetero)aromatic acids with potassium tert-butanolate and 19 substrates were synthesized(Scheme 1).b) Decarboxylative coupling reaction of CF3CH2 I with(hetero)aromatic carboxylatesA novel trifluoroethylation reaction of CF3CH2 I with(hetero)aromatic carboxylates via decarboxylative coupling reaction have been developed. Through screening catalyst, ligand, additive, solvent, reaction temperature and reaction time,we achieved the best reaction condition with PdCl2 as catalyst, PPh3 as ligand, Cul as additive, DMA as solvent, 150℃ for 4 h and 15 substrates were synthesized(Scheme2).2. Oxidation coupling reaction of allylalcohol with 3-pyridyl boric acids An efficient oxidation coupling reaction of allylalcohol with 3-pyridyl boricacids to synthesize β-(hetero)aryl ketones and aldehydes have been developed.Through screening catalyst, ligand, additive, solvent, reaction temperature and reaction time, we achieved the best reaction condition with Pd(OAc)2 as catalyst, BPy as ligand, Cu Cl as additive, DMSO as solvent, 80 ℃ for 12 h(Scheme 3).
Keywords/Search Tags:Decarboxylative coupling reaction, Trifluoroethylation reaction, Oxidation coupling reaction
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