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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

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Indole, ≥99%, FG

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Indole, ≥99%

Sigma-Aldrich

Copper, powder, <75 μm, 99%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.05mm, hard, 99.95+%

Copper, wire reel, 5m, diameter 1.0mm, as drawn, 99.99+%

Copper - O.F.H.C., foil, 6mm disks, thickness 1.0mm, half hard, 99.95+%

Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, annealed, 99.95+%

Copper - O.F.H.C., rod, 100mm, diameter 25.4mm, as drawn, 99.99+%

Copper - O.F.H.C., rod, 500mm, diameter 16mm, as drawn, 99.95+%

Copper - O.F.H.C., rod, 200mm, diameter 25.4mm, as drawn, 99.95+%

Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, hard, 99.95+%

Copper - O.F.H.C., rod, 200mm, diameter 12.7mm, as drawn, 99.95+%

Copper - O.F.H.C., foil, 8mm disks, thickness 0.1mm, hard, 99.95+%

Copper - O.F.H.C., foil, light tested, 50x50mm, thickness 0.010mm, hard, 99.95+%

Copper - O.F.H.C., foil, light tested, 100x100mm, thickness 0.075mm, half hard, 99.95+%

Copper - O.F.H.C., foil, 6mm disks, thickness 0.7mm, half hard, 99.95+%

Copper - O.F.H.C., foil, light tested, 100x100mm, thickness 0.010mm, hard, 99.95+%

Copper - O.F.H.C., rod, 1000mm, diameter 3.15mm, as drawn, 99.95+%