Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes: selective formation of phenanthrene derivatives.

doi:10.1021/jo501835u

Paper

Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes: selective formation of phenanthrene derivatives.

Published Sep 18, 2014 · T. Nagata, K. Hirano, T. Satoh

The Journal of organic chemistry

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42

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Abstract

2-Arylbenzoyl chlorides undergo annulative coupling with internal alkynes in the presence of a catalyst system of [IrCl(cod)]2/P(t-Bu)3 to selectively afford the corresponding phenanthrene derivatives accompanied by elimination of carbon monoxide and hydrogen chloride. The reaction occurs without addition of any external base. Deuterium-labeling experiments using 2-(d5-phenyl)benzoyl chloride suggest that the rate-determining step does not involve the C2'-H bond cleavage. Formation of a [(t-Bu)3PH][(biphenyl-2,2'-diyl)Ir(CO)Cl2] complex dimer, of which the structure was determined by single-crystal X-ray analysis, from a stoichiometric reaction at 60 °C without addition of alkyne also supports the facile C-H cleavage.

Study Snapshot

Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes selectively affords phenanthrene derivatives without external base addition, supporting facile C-H cleavage.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes: selective formation of phenanthrene derivatives.

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