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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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

Sigma-Aldrich

Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

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Indole, ≥99%

Sigma-Aldrich

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Indole, ≥99%, FG

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Copper, beads, 2-8 mm, 99.9995% trace metals basis

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Copper, beads, 2-8 mm, ≥99.99% trace metals basis

Copper, mesh, 100x100mm, nominal aperture 0.38mm, wire diameter 0.25mm, 40x40 wires/inch, open area 37%, plain weave mesh

Copper, wire reel, 5m, diameter 0.05mm, as drawn, 99.99+%

Copper - O.F.H.C., foil, 2m coil, thickness 0.05mm, annealed, 99.95+%

Copper, wire reel, 5m, diameter 0.25mm, as drawn, 99.99+%

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Copper, wire reel, 1000m, diameter 0.125mm, annealed, 99.9%

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Copper, wire reel, 500m, diameter 0.05mm, annealed, 99.9%

Copper, wire reel, 500m, diameter 0.125mm, annealed, 99.9%

Copper, wire reel, 5m, diameter 0.5mm, as drawn, 99.98+%

Copper, wire reel, 10m, diameter 0.5mm, annealed, 99.9%

Copper - O.F.H.C., foil, 20m coil, thickness 0.05mm, coil width 10mm, annealed, 99.95+%

Copper - O.F.H.C., foil, 25x25mm, thickness 0.25mm, annealed, 99.95+%