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

774111

Sigma-Aldrich

Copper, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

326437

Sigma-Aldrich

Copper, rod, diam. 3.1 mm, 99.999%

GF53102438

Copper, tube, 500mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%

GF10995914

Copper, tube, 100mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

GF95872225

Copper, tube, 200mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%

GF42838162

Copper, tube, 100mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF31266121

Copper, tube, 200mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF46565286

Copper, tube, 500mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF53626653

Copper, tube, 200mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF97831806

Copper, tube, 100mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

GF52673250

Copper, tube, 200mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF35241892

Copper, tube, 200mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%

GF73652250

Copper, tube, 500mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF37574523

Copper, tube, 200mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

GF91147495

Copper, tube, 500mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF51053699

Copper, tube, 100mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%

GF64429016

Copper, tube, 100mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF17777751

Copper, tube, 200mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%

GF35866761

Copper, tube, 200mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, as drawn, 99.9%

GF82636162

Copper, tube, 100mm, outside diameter 25.4mm, inside diameter 18.9mm, wall thickness 3.25mm, as drawn, 99.9%

GF80910323

Copper, tube, 200mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF40950222

Copper - O.F.H.C., foil, 10mm disks, thickness 0.010mm, hard, 99.95+%

GF23943898

Copper - O.F.H.C., foil, 6mm disks, thickness 0.05mm, hard, 99.95+%

GF31988098

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

GF12069176

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

GF80402587

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

GF29419498

Copper - O.F.H.C., foil, 2m coil, thickness 0.006mm, hard, 99.95+%

GF50855216

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

GF94205358

Copper - O.F.H.C., foil, 15mm disks, thickness 0.1mm, hard, 99.95+%