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

W259306

Sigma-Aldrich

Indole, ≥99%, FG

I3408

Sigma-Aldrich

Indole, ≥99%

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

326410

Sigma-Aldrich

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

349151

Sigma-Aldrich

Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

326488

Sigma-Aldrich

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

266744

Sigma-Aldrich

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

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

349224

Sigma-Aldrich

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

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%

326429

Sigma-Aldrich

Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

BCR058

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

349208

Sigma-Aldrich

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

GF77355579

Copper, tube, 1000mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%

GF89142701

Copper, tube, 1000mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

GF60058346

Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200

GF16694006

Copper, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

GF46821382

Copper, tube, 100mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF20661083

Copper, tube, 1000mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF00529040

Copper, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200

GF98886920

Copper, rod, 50mm, diameter 12.7mm, as drawn, 99.99+%

GF87182657

Copper, tube, 1000mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

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

GF68805760

Copper, wire reel, 50m, diameter 0.25mm, as drawn, 99.99+%

GF21709650

Copper, wire reel, 1000m, diameter 0.04mm, hard, 99.9%

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Copper, wire reel, 500m, diameter 0.125mm, annealed, 99.9%

GF74334809

Copper, wire reel, 2m, diameter 0.75mm, as drawn, 99.98+%