Chelation-assisted and steric-controlled selectivity in the Pd-catalyzed C-H/C-H oxidative coupling of indoles.

Chem Commun (Camb)

Organometallic Synthesis and Catalysis Lab, Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune - 411 008, India.

Published: November 2024

We report the first regioselective C2-C7 oxidative coupling of indoles using a palladium catalyst upon the strategic installation of -pyridinyl and C3-carbonyl, which delivers 2,7-biindoles with a broad scope (25 examples; up to 93% yield). Isolation of the catalytic intermediate reveals the initial activation of the C(7)-H bond, followed by the C(2)-H bond in indoles, and the reaction proceeds a Pd(II)/Pd(0) pathway.

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Source
http://dx.doi.org/10.1039/d4cc03835eDOI Listing

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