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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, shot, −3-+14 mesh, 99%

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

Copper (S, P), BCR^®, certified reference material, chips

Copper, IRMM^®, certified reference material, 0.1 mm foil

Copper, IRMM^®, certified reference material, 0.5 mm wire

Copper (O), BCR^®, certified reference material, rod

Copper - O.F.H.C., foil, 15mm disks, thickness 0.025mm, hard, 99.95+%

Copper, wire reel, 0.5m, diameter 0.25mm, as drawn, 99.99+%

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

Copper - O.F.H.C., foil, 5m coil, thickness 0.05mm, hard, 99.95+%

Copper - O.F.H.C., foil, 50mm disks, thickness 0.7mm, half hard, 99.95+%

Copper - O.F.H.C., foil, 2m coil, thickness 0.25mm, half hard, 99.95+%

Copper - O.F.H.C., foil, 25mm disks, thickness 0.006mm, hard, 99.95+%

Copper - O.F.H.C., foil, 1m coil, thickness 0.05mm, hard, 99.95+%

Copper - O.F.H.C., foil, 4mm disks, thickness 0.7mm, half hard, 99.95+%

Copper, tube, 500mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.9%

Copper, wire reel, 20m, diameter 0.25mm, annealed, 99.9%

Copper - O.F.H.C., foil, 4mm disks, thickness 0.5mm, half hard, 99.95+%

Copper - O.F.H.C., foil, 5m coil, thickness 0.006mm, hard, 99.95+%

Copper - O.F.H.C., foil, 5m coil, thickness 0.025mm, hard, 99.95+%

Copper - O.F.H.C., foil, 4mm disks, thickness 0.25mm, annealed, 99.95+%

Copper, wire reel, 10m, diameter 0.75mm, as drawn, 99.98+%

Copper - O.F.H.C., foil, 2m coil, thickness 0.1mm, hard, 99.95+%

Copper, wire reel, 2m, diameter 1.0mm, as drawn, 99.99+%

Copper, wire reel, 200m, diameter 0.075mm, annealed, 99.9%