Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes

Sapkota, Rishi R.; Tak, Raj Kumar; Aryal, Vivek; Niroula, Doleshwar; Secosky, Nicholas C.; Dhungana, Roshan K.; Giri, Ramesh

doi:10.1021/acs.orglett.2c02531

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“…Copper, with low toxicity and high catalytic activity, has received significant attention as a potential alternative to precious metals in synthesizing heterocycles through the C–H activation and functionalization processes . In this context, Cu-catalyzed one-pot sequential methods for various indole syntheses have also been developed, including (a) Ullmann-type C–N formation and cross-dehydrogenative coupling (CDC) reactions, (b) Chan–Lam and CDC reactions, (c) hydroamination and oxidative cyclization reactions, (d) hydroamination and CDC reactions, and (e) cyclization/coupling of alkenyl aldimines with arylzinc reagents . Recently, we developed a tandem strategy for selective 2-substituted indole synthesis by Pd-catalyzed reductive cyclization of 1-halo-2-nitroarenes with terminal alkynes .…”

Section: Introductionmentioning

confidence: 99%

Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C–H Annulation

2023

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A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds has been developed. The present protocol involves copper-mediated tandem hydroamination followed by C–H annulation of unprotected anilines with a wide range of internal alkynes. In the presence of Cu(OAc)2·H2O and trifluoroacetic acid (TFA), the reaction proceeds well to afford a variety of substituted indole derivatives in moderate to good yields. This process was found to be compatible with both primary and secondary anilines coupled with aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, revealing the cost-effectiveness and environmentally benign feature of the current protocol.

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Section: Introductionmentioning

confidence: 99%

Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C–H Annulation

2023

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show abstract

Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes

Abstract: We report a Cu(II)-catalyzed cyclization/coupling of alkenyl aldimines with arylzinc reagents to create indole-3-diarylmethane derivatives (Sapkota et al. ChemRxiv 2022,

Cited by 1 publication

References 64 publications

Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C–H Annulation

Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C–H Annulation

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