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Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamides and aryl boronic acids.

Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamides and aryl boronic acids.

Organic letters (2014-06-25)

Jing Zheng, Yan Zhang, Sunliang Cui

RÉSUMÉ

A Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamide and aryl boronic acids is reported. The coupling is mild and efficient toward diverse product formation, with selective C-C and C-C/C-N bond formation. Kinetic isotope effects studies were conducted to reveal a mechanism of C-H activation and electrophilic addition.

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Sigma-Aldrich

Indole, ≥99%

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Copper, powder, 99.999% trace metals basis

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Copper, foil, thickness 0.25 mm, 99.98% trace metals basis

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Copper, powder, <425 μm, 99.5% trace metals basis

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Copper, tube, 500mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

Copper, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

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