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Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions.

ABSTRACT: A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the biscoupled products showed a maximum of emission in the violet region of the spectrum.

SUBMITTER: Lechel T

PROVIDER: S-EPMC2874341 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions.

Lechel Tilman T Brüdgam Irene I Reissig Hans-Ulrich HU

Beilstein journal of organic chemistry 20100429

A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the b ...[more]

PMID: 20502600

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