Electrooxidative Iridium-Catalyzed Regioselective Annulation of Benzoic Acids with Internal Alkynes

Organic Letters, Journal Year: 2021, Volume and Issue: 23(4), P. 1209 - 1215

Published: Feb. 4, 2021

Electrochemically driven, Cp*Ir(III)-catalyzed regioselective annulative couplings of benzoic acids with alkynes have been established herein. The combination iridium catalyst and electricity not only circumvents the need for stoichiometric amount chemical oxidant, but also ensures broad reaction compatibility a wide array sterically electronically diverse substrates. This electrochemical approach represents sustainable strategy as an ideal alternative supplement to oxidative annulations methodology be engaged in synthesis isocoumarin derivatives.

Language: Английский

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Hydroxyl-Directed Rh(III)-Catalyzed C–H Functionalization: Access to Benzo[de]chromenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1622 - 1627

Published: March 3, 2023

A cascade oxidative annulation reaction of heterocyclic ketene aminals (HKAs) with internal alkynes catalyzed by [Cp*RhCl2]2 and oxidized Cu(OAc)2·H2O was developed to efficiently synthesize highly functionalized benzo[de]chromene derivatives in good excellent yields. The proceeded the sequential cleavage C(sp2)-H/O-H C(sp2)-H/C(sp2)-H bonds. These multicomponent reactions were regioselective. In addition, all products exhibited intense fluorescence emission solid state, they demonstrated concentration-dependent quenching presence Fe3+, indicating that these compounds could be used recognition Fe3+.

Language: Английский

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Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

Advanced Materials, Journal Year: 2023, Volume and Issue: 35(49)

Published: March 25, 2023

Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses largely relied on multistep approaches or the conventional Scholl reaction. However, reactions are inefficient with electron-deficient substrates, require stoichiometric chemical oxidants, typically occur presence strong acid. In sharp contrast, electrochemistry has gained considerable momentum during past decade an alternative for facile straightforward assembly, generally via electro-oxidative dehydrogenative annulation, releasing molecular hydrogen sole byproduct by evolution This review provides overview recent significant advances field electrochemical various until January 2023.

Language: Английский

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Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles

ACS Omega, Journal Year: 2023, Volume and Issue: 8(7), P. 6175 - 6217

Published: Feb. 1, 2023

Numerous applications in the realm of biological exploration and drug synthesis can be found heterocyclic chemistry, which is a vast subject. Many efforts have been developed to further improve reaction conditions access this interesting family prevent employing hazardous ingredients. In instance, it has stated that green environmentally friendly manufacturing methodologies introduced create N-, S-, O-heterocycles. It appears one most promising methods these types compounds avoiding use stoichiometric amounts oxidizing/reducing species or precious metal catalysts, only catalytic are sufficient, represent an ideal way contributing toward resource economy. Thus, renewable electricity provides clean electrons (oxidant/reductant) initiate cascade via producing reactive intermediates facilitate building new bonds for valuable chemical transformations. Moreover, electrochemical activation using metals as mediators identified more efficient strategy selective functionalization. indirect electrolysis makes potential range practical, less side reactions occur. The latest developments electrolytic O-heterocycles main topic mini review, was documented over last five years.

Language: Английский

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Modern photo- and electrochemical approaches to aryl radical generation

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5232 - 5277

Published: Jan. 1, 2024

This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.

Language: Английский

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