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

I3408

Sigma-Aldrich

Indole, ≥99%

326488

Sigma-Aldrich

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

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

W259306

Sigma-Aldrich

Indole, ≥99%, FG

254177

Sigma-Aldrich

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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

GF11113142

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

GF38786912

Copper, wire reel, 1m, diameter 1.0mm, as drawn, 99.99+%

GF55232894

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

GF46341783

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

GF11467155

Copper, wire reel, 20m, diameter 0.5mm, as drawn, 99.999%

GF41393202

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

GF42873723

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

GF03331268

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

GF73649559

Copper, wire reel, 10m, diameter 1.0mm, annealed, 99.9%

GF84372521

Copper, tube, 200mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF41636921

Copper, tube, 100mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.9%

GF52128008

Copper, wire reel, 100m, diameter 0.1mm, annealed, 99.9%

GF65635229

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

GF23409491

Copper - O.F.H.C., foil, 10mm disks, thickness 0.05mm, hard, 99.95+%

GF04615860

Copper, tube, 200mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.9%

GF48509242

Copper, wire reel, 500m, diameter 0.25mm, annealed, 99.9%

GF16236738

Copper - O.F.H.C., foil, 10mm disks, thickness 0.025mm, hard, 99.95+%

GF23476833

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

GF82471620

Copper, wire reel, 100m, diameter 1.0mm, annealed, 99.9%

GF35012584

Copper, wire reel, 250m, diameter 0.04mm, annealed, 99.9%

GF14011647

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

GF22218847

Copper, tube, 500mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%