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

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326488

Sigma-Aldrich

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349208

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349216

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Copper, wire, diam. 1.0 mm, ≥99.9%

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349224

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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

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207780

Sigma-Aldrich

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Sigma-Aldrich

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61139

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GF23864463

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GF92323166

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