Thallium in organic synthesis. 46. Oxidative coupling of aromatic compounds using thallium(III) trifluoroacetate. Synthesis of biaryls

Abstract

Treatment of a variety of aromatic compounds with thallium(II1) trifluoroacetate in trifluoroacetic acid, carbon tetrachloride, or acetonitrile results in oxidative coupling to give symmetrical biaryls in good to excellent yield.

Investigation of axial anionic ligand and porphyrin substituent effects on the oxidation of iron(III) porphyrins: porphyrin-centered vs. metal-centered oxidation

“…1976, 16, 213. (18) Fuhrop, J.-H.; Smith, K. M. In "Porphyrins and Metalloporphyrins"; Smith, K. M., Ed. ; Elsevier: Amsterdam, 1975; pp 765-769.…”

Mild, Fast, and Easy To Conduct MoCl5-Mediated Dehydrogenative Coupling Reactions in Flow

“…Dehydrogenative or oxidative coupling reactions have emerged as a powerful methodology to form new C–C bonds between arenes . While thallium­(III) reagents have been applied in the past, today more environmentally friendly reagents such as iron­(III) chloride, molybdenum­(V) chloride, bis­(trifluoroacetoxy) iodobenzene (PIFA), and 2,3-dichloro-5,6-dicycano-1,4-benzoquinone (DDQ)/methanesulfonic acid are described in this context . In particular, MoCl 5 exhibits high performance in establishing new C–C and C–S bonds, respectively.…”

An economical synthesis of the alkaloids, 3,4-dimethoxy-ω-(2-piperidyl)-acetophenone, julandine, and cryptopleurine

“…Thallium(m) trifluoroacetate has recently found application as an efficient coupling reagent for biarylslo and its use in the conversion of septicine (7) into tylophorine (9) has been noted above. The transformation of julandine (8) into cryptopleurine (10) was achieved similarly even though the linkage to ring B is notably meta to the methoxysubstituent [l mol. equiv.…”