Cited by Silver-catalyzed radical bisphosphonation reaction of maleimides with diarylphosphine oxides

Alkyne Insertion Enabled Vinyl to Acyl 1,5‐Palladium Migration: Rapid Access to Substituted 5‐Membered‐Dihydrobenzofurans and Indolines DOI

Mingruo Ding,

Pengcheng Ou,

Xuening Li

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(18)

Published: Feb. 21, 2023

"Through space" palladium/hydrogen shift is an efficient strategy to achieve selective functionalization of a specific remote C-H bond. Compared with relatively extensive exploited 1,4-palladium migration process, the relevant 1,5-Pd/H was far less investigated. We herein report novel pattern between vinyl and acyl group. Through pattern, rapid access 5-membered-dihydrobenzofuran indoline derivatives has been achieved. Further studies have unveiled unprecedented trifunctionalization (vinylation, alkynylation amination) phenyl ring through 1,5-palladium relayed decarbonylative Catellani type reaction. A series mechanistic investigations DFT calculations provided insights into reaction pathway. Notably, it that in our case prefers stepwise mechanism involving PdIV intermediate.

Language: Английский

Citations

Recent advances in electrochemical C—H phosphorylation DOI

Yulia H. Budnikova,

Egor L. Dolengovsky,

Maxim V. Tarasov

et al.

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Nov. 3, 2022

The activation of C–H bond, and its direct one-step functionalization, is one the key synthetic methodologies that provides access to a variety practically significant compounds. Particular attention focused on modifications obtained at final stages synthesis complicated molecules, which requires high tolerance presence existing functional groups. Phosphorus an indispensable element life, phosphorus chemistry now experiencing renaissance due new emerging applications in medicinal chemistry, materials (polymers, flame retardants, organic electronics, photonics), agricultural (herbicides, insecticides), catalysis (ligands) other important areas science technology. In this regard, search for new, more selective, low-waste routes become relevant. context, electrosynthesis has proven be eco-efficient convenient approach many respects, where reagents are replaced by electrodes, reactants applied potential determines their “oxidizing or reducing ability”. An electrochemical such processes being developed rapidly demonstrates some advantages over traditional classical methods C-H phosphorylation. main reasons success exclusion excess from reaction system: as oxidants, agents, sometimes metal and/or improvers, challenge isolation, increase wastes reduce yield frequent incompatibility with these Ideal conditions include electron reactant (regulated potential) by-products hydrogen hydrocarbon. review summarizes analyzes achievements preparation various derivatives carbon-phosphorus bonds, collects data redox properties most commonly used precursors. Electrochemically induced reactions both without catalyst metals, competitive oxidation precursors leads either bond generation phosphorus-centered radicals (radical cations) states will examined. focuses publications past 5 years.

Language: Английский

Citations

Advances in Palladium-Catalyzed C(sp³)–H Functionalization: The Role of Traceless Directing Groups DOI

Masoud Sadeghi

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 15356 - 15373

Published: Oct. 3, 2024

Language: Английский

Citations

Regioselective C–H Active Carbonylation via 1,4-Palladium Migration DOI

Ming Li,

Shun‐Xi Li,

Dong‐Ping Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2761 - 2766

Published: April 13, 2023

We report a highly regioselective three-component coupling reaction of styrene, CO gas, and an amine compound to synthesize multisubstituted α,β-unsaturated amides, which involves palladium-catalyzed sequential 1,4-palladium migration, C(sp2)-H activation, carbonylation, amination. Salient features this strategy include the use 1 atm CO, excellent stereochemistry, good functional group tolerance. Further, series control experiments density theory calculations were performed afford some insights for transfer mechanism.

Language: Английский

Citations

1,4-Pd Migration-Enabled Synthesis of Fused 4-Membered Rings DOI

Μαρία Τσιτοπούλου,

Antonin Clemenceau, Pierre Thesmar

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(28), P. 18811 - 18816

Published: July 5, 2024

1,4-Palladium migration has been widely used for the functionalization of remote C–H bonds. However, this mechanism limited to aryl halide precursors. This work reports an unprecedented Pd0-catalyzed cyclobutanation protocol producing valuable fused cyclobutanes starting from cycloalkenyl (pseudo)halides. reaction takes place via alkenyl-to-alkyl 1,4-Pd migration, followed by intramolecular Heck coupling. The method performs best with cyclohexenyl precursors, giving access a variety substituted bicyclo[4,2,0]octenes. Reactants containing N-methyl or methoxy group give rise azetidines oxetanes, respectively, same mechanism. Kinetic and deuterium-labeling studies point rate-limiting C(sp3)–H activation step.

Language: Английский

Citations

Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with H‐Phosphonates and H‐Phosphine Oxides DOI

Jingjing He,

Zhudi Sun,

Yupian Deng

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 22, 2023

Abstract Efficient synthesis of β‐hydroxy‐β‐CF 3 ‐phosphonates and ‐phosphine oxides by Mn‐mediated or transition‐metal‐free hydroxyphosphorylation α‐trifluoromethy)styrenes with H the assistance air, respectively, was described.

Language: Английский

Citations

Solvent-Switchable Remote C–H Activation via 1,4-Palladium Migration Enables Site-Selective C–P Bond Formation: A Tool for the Synthesis of P-Chiral Phosphinyl Imidazoles DOI

Ifenna I. Mbaezue, Shiguang Li, Angula Chandra Shekar Reddy

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4200 - 4204

Published: May 13, 2024

Solvent-switchable and site-selective phosphorylation of imidazoles at the C2 or C5 position imidazole ring was achieved via 1,4-palladium migration.

Language: Английский

Citations

C(sp3) P cross-coupling of alkyl substrates with P(O) H compounds and phosphites DOI

Jinyu Tang,

Jinxuan Ni,

Qian Chen

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 149, P. 155266 - 155266

Published: Aug. 22, 2024

Language: Английский

Citations

Taming the Selective C−H Bond Activation through 1,5‐Palladium Migration DOI

Yaru Fang,

Mingruo Ding,

Xueliang Huang

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(5)

Published: Nov. 29, 2023

Abstract “Through space” metal/hydrogen shift constitutes one of the efficient elementary step in organometallic chemistry to achieve selective remote C−H bond functionalization. Compared with relatively extensive exploration on 1,4‐palladium migration, processes corresponding 1,5‐palladium translocation are far less explored. Based our understanding related research areas, we summarized advances achieved activation through a key migration this minireview. The background, reaction scope, and more importantly, mechanistic rationale each transformation was discussed. We hope by reading minireview, could get general perspective direct via 1,5‐palladium/hydrogen shift, understand why such process is common when compared going 1,4‐palladium/hydrogen eventually be inspired develop practical ways for synthesis valuable molecules, which not prepared easily other traditional approaches.

Language: Английский

Citations

Recent Progress in Metal-Catalyzed C(sp³)-P Bond Formation DOI

Jia‐Lin Tu, Zhengjia Shen, Binbin Huang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 168, P. 134352 - 134352

Published: Nov. 1, 2024

Language: Английский

Citations