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

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

Sigma-Aldrich

吲哚, ≥99%

Sigma-Aldrich

铜, foil, thickness 0.25 mm, 99.98% trace metals basis

Sigma-Aldrich

铜, powder, 99.999% trace metals basis

Sigma-Aldrich

铜, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

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

Sigma-Aldrich

铜, powder, <75 μm, 99%

Sigma-Aldrich

铑, powder, 99.95% trace metals basis

Sigma-Aldrich

铜, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis

Sigma-Aldrich

铜, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis

Sigma-Aldrich

铜, powder (spheroidal), 10-25 μm, 98%

Sigma-Aldrich

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

Sigma-Aldrich

铜, turnings, purum p.a., ≥99.0%

Sigma-Aldrich

吲哚, ≥99%, FG

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

铜, foil, ≥99.8% (complexometric)

铜, tube, 100mm, outside diameter 3.5mm, inside diameter 1.56mm, wall thickness 0.97mm, as drawn, 99.9%

Sigma-Aldrich

铜, bars (random sizes), ≥99.999% trace metals basis

Supelco

吲哚, analytical standard

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

铜, shot, −3-+14 mesh, 99%

Sigma-Aldrich

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

Sigma-Aldrich

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

铜, foil, 100x100mm, thickness 0.125mm, hard, 99.95+%

Sigma-Aldrich

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

连续铸铜 (O), BCR^®, certified reference material, rod

Sigma-Aldrich

铜, sputtering target, diam. × thickness 2.00 in. × 0.25 in., 99.95% trace metals basis