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

254177

Sigma-Aldrich

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

BCR058

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

326410

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

266744

Sigma-Aldrich

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

GF80997889

Copper - O.F.H.C., foil, 1m coil, thickness 0.010mm, coil width 25mm, hard, 99.95+%

GF58516285

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

GF24248864

Copper - O.F.H.C., foil, 2m coil, thickness 0.20mm, hard, 99.95+%

GF93757786

Copper - O.F.H.C., foil, 15mm disks, thickness 0.125mm, hard, 99.95+%

GF10253179

Copper - O.F.H.C., foil, 25mm disks, thickness 0.7mm, half hard, 99.95+%

GF14058705

Copper, wire reel, 0.5m, diameter 0.5mm, as drawn, 99.999%

GF18312791

Copper, wire reel, 100m, diameter 0.02mm, hard, 99.99+%

GF96137837

Copper - O.F.H.C., foil, 25mm disks, thickness 1.0mm, half hard, 99.95+%

GF03331268

Copper, tube, 500mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF11113142

Copper, tube, 500mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

GF28659471

Copper, wire reel, 0.2m, diameter 1.0mm, as drawn, 99.99+%

GF43853148

Copper - O.F.H.C., foil, 2m coil, thickness 0.7mm, half hard, 99.95+%

GF32166761

Copper - O.F.H.C., foil, 5m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

GF51978437

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

GF46297468

Copper, tube, 500mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF69818855

Copper - O.F.H.C., foil, 50mm disks, thickness 0.05mm, hard, 99.95+%

GF08771766

Copper - O.F.H.C., foil, 1m coil, thickness 0.1mm, half hard, 99.95+%

GF99677165

Copper, wire reel, 1000m, diameter 0.05mm, annealed, 99.9%

GF14011647

Copper, tube, 500mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%

GF77248772

Copper - O.F.H.C., foil, 5m coil, thickness 0.010mm, hard, 99.95+%

GF32269259

Copper - O.F.H.C., foil, 4mm disks, thickness 0.010mm, hard, 99.95+%

GF58362048

Copper - O.F.H.C., foil, 5m coil, thickness 0.1mm, half hard, 99.95+%

GF25261657

Copper - O.F.H.C., foil, 1m coil, thickness 0.05mm, coil width 10mm, annealed, 99.95+%

GF81594399

Copper, wire reel, 100m, diameter 0.5mm, annealed, silver plated, 99.9%