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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

Indole, ≥99%

Sigma-Aldrich

Copper, foil, thickness 0.025 mm, 99.98% trace metals basis

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

Copper, wire, diam. 2.0 mm, 99.999% trace metals basis

Sigma-Aldrich

Copper, wire, diam. 0.64 mm, 99.995% trace metals basis

Sigma-Aldrich

Indole, ≥99%, FG

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

Sigma-Aldrich

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

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

Continuous cast copper (O), BCR^®, certified reference material, rod

Sigma-Aldrich

Copper, powder, <75 μm, 99%

Sigma-Aldrich

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

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

Copper, wire reel, 5000m, diameter 0.04mm, annealed, 99.9%

Copper, wire reel, 200m, diameter 0.5mm, annealed, silver plated, 99.9%

Copper, wire reel, 100m, diameter 0.05mm, annealed, 99.9%

Copper, wire reel, 0.2m, diameter 0.1mm, aluminum cladding, outside diameter 0.25mm, 99.9%

Copper, wire reel, 20m, diameter 0.5mm, annealed, silver plated, 99.9%

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

Copper, wire reel, 500m, diameter 0.5mm, annealed, 99.9%

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

Copper, wire reel, 500m, diameter 0.5mm, as drawn, 99.98+%

Copper, wire reel, 100m, diameter 0.5mm, as drawn, 99.98+%

Copper, wire reel, 50m, diameter 0.04mm, annealed, 99.9%

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

Copper, wire reel, 25m, diameter 0.75mm, as drawn, 99.98+%

Copper, wire reel, 5m, diameter 0.5mm, annealed, silver plated, 99.9%

Copper, tube, 200mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

Copper, tube, 200mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%