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

357456

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

266086

Sigma-Aldrich

Copper, powder, <425 μm, 99.5% trace metals basis

326437

Sigma-Aldrich

Copper, rod, diam. 3.1 mm, 99.999%

311405

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

326453

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

BCR017B

Copper (S, P), BCR^®, certified reference material, chips

IRMM522A

Copper, IRMM^®, certified reference material, 0.1 mm foil

IRMM522C

Copper, IRMM^®, certified reference material, 0.5 mm wire

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

203122

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

GF91364362

Copper - O.F.H.C., foil, 2m coil, thickness 0.010mm, hard, 99.95+%

GF43015430

Copper - O.F.H.C., foil, 6mm disks, thickness 0.025mm, hard, 99.95+%

GF10995914

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

GF70352243

Copper - O.F.H.C., foil, 4mm disks, thickness 0.25mm, annealed, 99.95+%

GF84497125

Copper - O.F.H.C., foil, 150x150mm, thickness, 0.5mm, half hard, flattened, 99.95+%

GF29520963

Copper, tube, 200mm, outside diameter 25.4mm, inside diameter 18.9mm, wall thickness 3.25mm, as drawn, 99.9%

GF51897268

Copper, tube, 200mm, outside diameter 1.0mm, inside diameter 0.24mm, wall thickness 0.38mm, as drawn, 99.9%

GF27751967

Copper - O.F.H.C., foil, 1m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

GF94205358

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

GF17777751

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

GF60882183

Copper - O.F.H.C., foil, 5m coil, thickness 0.010mm, coil width 25mm, hard, 99.95+%

GF41548462

Copper - O.F.H.C., foil, 1m coil, thickness 0.05mm, coil width 300mm, half hard, 99.95+%

GF17162232

Copper - O.F.H.C., foil, 4mm disks, thickness 0.25mm, half hard, 99.95+%

GF11950062

Copper - O.F.H.C., foil, 10mm disks, thickness 0.125mm, hard, 99.95+%

GF91776459

Copper - O.F.H.C., foil, 20m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

GF71992053

Copper - O.F.H.C., foil, 4mm disks, thickness 0.5mm, half hard, 99.95+%

GF47255362

Copper - O.F.H.C., foil, 2m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

GF90925735

Copper - O.F.H.C., foil, 1m coil, thickness 0.20mm, hard, 99.95+%

GF95872225

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

GF09072031

Copper - O.F.H.C., foil, 15mm disks, thickness 0.7mm, half hard, 99.95+%