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
RESUMO

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.

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Sigma-Aldrich
Indole, ≥99%
Sigma-Aldrich
Copper, powder, <425 μm, 99.5% trace metals basis
Sigma-Aldrich
Copper, powder, 99.999% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 0.25 mm, 99.98% trace metals basis
Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Sigma-Aldrich
Copper, wire, diam. 1.0 mm, ≥99.9%
Sigma-Aldrich
Copper, powder, <75 μm, 99%
Sigma-Aldrich
Copper, powder (spheroidal), 10-25 μm, 98%
Sigma-Aldrich
Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%
Sigma-Aldrich
Copper, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis
Sigma-Aldrich
Copper, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis
Sigma-Aldrich
Copper, electrolytic, Analytical Reagent, reag. Ph. Eur., ≥99.9% (complexometric), wire
Sigma-Aldrich
Indole, ≥99%, FG
Sigma-Aldrich
Copper, foil, thickness 0.025 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 1.0 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, powder (dendritic), <45 μm, 99.7% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 0.5 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, turnings, purum p.a., ≥99.0%
Supelco
Indole, analytical standard
Sigma-Aldrich
Copper, foil, ≥99.8% (complexometric)
Sigma-Aldrich
Copper, wire, diam. 0.25 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, beads, 2-8 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Copper, beads, 2-8 mm, 99.9995% trace metals basis
Supelco
Indole solution, 2000 μg/mL in methanol, certified reference material
Sigma-Aldrich
Copper, wire, diam. 2.0 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, wire, diam. 0.64 mm, 99.995% trace metals basis
Copper - O.F.H.C., foil, 150x150mm, thickness 0.20mm, hard, 99.95+%
Copper, wire reel, 100m, diameter 0.05mm, annealed, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, 12mm disks, thickness 0.5mm, as rolled, 99.9%

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