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

BCR058

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

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

326488

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

349151

Sigma-Aldrich

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349224

Sigma-Aldrich

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

326410

Sigma-Aldrich

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

254177

Sigma-Aldrich

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

266744

Sigma-Aldrich

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

W259306

Sigma-Aldrich

Indole, ≥99%, FG

326429

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

I3408

Sigma-Aldrich

Indole, ≥99%

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

GF97882835

Copper - O.F.H.C., sheet, 100x100mm, thickness 4.76mm, 99.95+%

GF33500607

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GF27357240

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.075mm, half hard, 99.95+%

GF58595675

Copper - O.F.H.C., tube, 200mm, outside diameter 1.23mm, inside diameter 0.51mm, wall thickness 0.36mm, 99.95+%

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

GF39253721

Copper - O.F.H.C., sheet, 50x50mm, thickness 4.76mm, 99.95+%

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Copper - O.F.H.C., tube, 500mm, outside diameter 0.635mm, inside diameter 0.275mm, wall thickness 0.18mm, 99.95+%

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