Electrochemical Regioselective Cross-Dehydrogenative Coupling of Indoles with Xanthenes

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(2), P. 1056 - 1064

Published: Dec. 29, 2021

An electrochemical cross-dehydrogenative coupling of indoles with xanthenes has been established at room temperature. This reaction could proceed in the absence any catalyst or external oxidant, and generate indole derivatives moderate yields. Mechanistic experiments support that a radical pathway maybe involved this system.

Language: Английский

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Phosphorylation of arenes, heteroarenes, alkenes, carbonyls and imines by dehydrogenative cross-coupling of P(O)–H and P(R)–H

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 20(3), P. 498 - 537

Published: Nov. 23, 2021

Organophosphorous compounds have recently emerged as a powerful class of with widespread applications, such in bioactive natural products, pharmaceuticals, agrochemicals and organic materials, ligands catalysis. The preparation these requires synthetic techniques novel catalytic systems varying from transition metal, photo- electrochemical catalysis to transformations without metal catalysts. Over the past few decades, addition P-H bonds alkenes, alkynes, arenes, heteroarenes other unsaturated substrates hydrophosphination related reactions via above-mentioned processes has an atom economical approach obtain organophosphorus compounds. In most cycles, bond is cleaved yield phosphorus-based radical, which adds onto substrate followed by reduction corresponding radical yielding product.

Language: Английский

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Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

ChemSusChem, Journal Year: 2023, Volume and Issue: 16(12)

Published: March 7, 2023

Electrochemically promoted transition metal-catalyzed C-H functionalization has emerged as a promising area of research over the last few decades. However, development in this field is still at an early stage compared to traditional reactions using chemical-based oxidizing agents. Recent reports have shown increased attention on electrochemically functionalization. From standpoint sustainability, environmental friendliness, and cost effectiveness, oxidation metal catalyst offers mild, efficient, atom-economical alternative chemical oxidants. This Review discusses advances metal-electrocatalyzed past decade describes how unique features electricity enable economic sustainable way.

Language: Английский

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Electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: June 17, 2022

Abstract Metallocenes are privileged backbones for synthesis and catalysis. However, the direct dehydrogenative C−H functionalization of unsymmetric metallocenes suffers from reactivity selectivity issues. Herein, we report an electrochemically driven regioselective phosphorylation group 8 metallocenes. Mechanistic investigations indicate this cross coupling occurs through electrophilic radical substitution metallocene with a phosphoryl radical, facilitated by itself. This work not only offers efficient divergent phosphorylated metallocenes, but also provides guide to interpret regioselectivity

Language: Английский

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Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10967 - 10981

Published: July 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Language: Английский

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