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%

349224

Sigma-Aldrich

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

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

W259306

Sigma-Aldrich

Indole, ≥99%, FG

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

254177

Sigma-Aldrich

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

326410

Sigma-Aldrich

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

326429

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

349151

Sigma-Aldrich

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

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

326488

Sigma-Aldrich

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

BCR058

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

GF21744952

Copper, insulated wire, 20m, conductor diameter 0.125mm, insulation thickness 0.002mm, 2 micron polyesterimide insulation, 99.9%

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%

GF16694006

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

GF23864463

Copper, tube, 1000mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF53474980

Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF93436926

Copper, tube, 1000mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF42937768

Copper - O.F.H.C., foil, 1m coil, thickness 0.25mm, half hard, 99.95+%

GF98944600

Copper - O.F.H.C., foil, 25mm disks, thickness 0.025mm, hard, 99.95+%

GF93055901

Copper - O.F.H.C., foil, 2m coil, thickness 0.025mm, hard, 99.95+%

GF94804779

Copper - O.F.H.C., foil, 50mm disks, thickness 0.25mm, half hard, 99.95+%

GF07953644

Copper - O.F.H.C., foil, 10mm disks, thickness 0.1mm, hard, 99.95+%

GF65221512

Copper - O.F.H.C., foil, 5m coil, thickness 0.05mm, coil width 300mm, half hard, 99.95+%

GF17037031

Copper - O.F.H.C., foil, 10mm disks, thickness 0.075mm, half hard, 99.95+%

GF14058705

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