Synthesis, Год журнала: 2023, Номер 56(11), С. 1719 - 1726
Опубликована: Июнь 27, 2023
Abstract Deoxygenative alkylation of benzyl alcohols was realized by using acetate as the alcohol activation group. The C–O bond homolysis is achieved a boryl radical-promoted β-scission process. strategy amenable to variety alcohols, including primary, secondary, and more challenging tertiary alcohols. synthetic practicability demonstrated gram-scale one-pot reaction.
Язык: Английский
ACS Catalysis, Год журнала: 2024, Номер 14(9), С. 6451 - 6461
Опубликована: Апрель 12, 2024
Given the abundance of alcohol feedstocks and significance disulfides, we herein report a nickel-catalyzed direct deoxygenative disulfuration alcohols with trisulfide dioxides to access wide range disulfide molecules without cumbersome decoration coupling partners. The use readily available dicyclohexylcarbodiimide form transient isoureas provides activation high bond dissociation energy C–O bond, which facilitates straightforward conversion nonderivatized forge C–SS bond. Notably, this method obviates preactivation multistep procedure catalytic turnover under exogenous ligand base-free conditions, featuring broad substrate scope functional group compatibility. It thus offers robust alternative existing methods for precise construction versatile compounds from more abundant commercially substrates. synthetic utility was further showcased by successful gram-scale experiments structurally complex pharmaceuticals.
Язык: Английский
Процитировано
12
ACS Catalysis, Год журнала: 2024, Номер 14(17), С. 13451 - 13496
Опубликована: Авг. 26, 2024
Alcohols are abundant with versatile structural variety and have ample use as pivotal functional groups in numerous organic processes. Because of their frequent occurrence enumerable natural products, bioactive molecules, medicinal components, alcohol functionalities provide a promising scope research to advance the operational diversity for improving clinical success. Recent years witnessed design modern C–C C–heteroatom bond-forming approaches easily accessible commercially available unactivated aliphatic alcohols native adaptive sp3 handles, hence offering groundbreaking transformative pathways functionalization complex molecular architectures. The judicial application appropriate activating generate alkyl radical from through C–O bond fragmentation employ it potential alkylating agent unfolds unique synthetic strategies, thereby replacing obvious requirement halides. This review elaborately discusses recent trends regarding using C(sp3)-centered various chemical transformations by exploiting different activation modes disrupter under photoredox catalysis. presentation is organized nature scaffolds, kind formation, progress achieved this domain since original discovery providing illustrative examples mechanistic details, focus on difficulties future prospects.
Язык: Английский
Процитировано
10
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3975 - 3980
Опубликована: Фев. 27, 2023
A visible-light-driven deoxygenative cross-coupling of alcohols with sulfonyl oxime ethers has been developed by using xanthate salts as alcohol-activating groups. Upon convenient generation and direct photoexcitation anions, a broad range including primary ones can efficiently undergo this transformation to afford diverse derivatives. This one-pot protocol features mild conditions, substrate scope, late-stage applicability, without the need for any external photocatalysts or electron donor-acceptor complex formation.
Язык: Английский
Процитировано
20
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6334 - 6344
Опубликована: Апрель 15, 2024
A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.
Язык: Английский
Процитировано
6
Organic Letters, Год журнала: 2023, Номер 25(35), С. 6571 - 6576
Опубликована: Авг. 30, 2023
A practical and precise method for visible-light-promoted deoxygenative deuteration of common aliphatic alcohols using D2O as the deuterium source is reported. Upon intermediacy xanthate anions, a variety primary, secondary, tertiary can be facilely transformed into deuterioalkanes with excellent D-incorporation at predicted sites. The deoxygenation sequence catalyzed by in situ formed deuterated 2-mercaptopyridine, which plays dual roles atom transfer catalyst an electron shuttle well.
Язык: Английский
Процитировано
12
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3629 - 3634
Опубликована: Фев. 16, 2024
The visible-light-promoted deoxygenative radical heteroarylation of alcohols was achieved in the absence any external photosensitizers. processes occur through generation xanthate salts from alcohols, followed by SET and fragmentation, delivering alkyl radicals to react with heteroaryl sulfones. This method is amenable for a wide range good functional group tolerance, providing practical strategy alkylation benzo-heteroaromatics. Mechanism studies indicate that direct visible-light excitation anions subsequent initiate reactions.
Язык: Английский
Процитировано
4
Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS 2 has been developed using xanthate salts as alkyl radical precursors in the presence tricyclohexylphosphine.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 14, 2025
This study proposes a green and efficient atom- step-economical method for converting hazardous CS2 to dithiocarbamate derivatives under visible light irradiation catalyst-free conditions. By the construction of novel C-S C-N bonds, series β-dicarbonyl compounds amines are incorporated into products. Under light, amine first form bis(dialkylaminethiocarbonyl)disulfides, which then react with K2CO3-activated electron donor-acceptor (EDA) complexes subsequently generate target confirms time that bis(dialkylaminethiocarbonyl)disulfides can act as acceptors an EDA complex compounds, coupled product light.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Фев. 26, 2025
Herein, we report a photocatalytic redox-neutral and reductive deoxygenative alkylation of N-acyl carbamothioates from benzylic alcohols, with substituted Hantzsch esters allylic sulfones to afford unsymmetrical 1,2-diaryl ethanes allylarylmethanes, respectively. This protocol facilitates facile deoxyalkylation primary, secondary, tertiary alcohol-derived carbamothioates, which features mild reaction conditions, broad functional group tolerance, the obviation external S/O trapping reagents as well transition metal-coupling catalysts.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Май 31, 2025
Imino-sulfonylation of styrene represents a powerful method for constructing highly functionalized molecules, while only diphenyl imines were able to be employed in previous reports. By modulating the electron property styrene, visible-light-mediated radical/radical cross-coupling aldiminyl radical and carbon-centered was achieved synthesize diverse aldimine-embedded sulfones by using sulfonyl aldimines α-trifluoromethylstyrenes. One-pot oxidation delivered Ritter-type amidation products without need excessive nitriles as solvent. Furthermore, this protocol took advantage simple reaction conditions, good substituent diversity, high atom economy broaden research radicals amination alkenes.
Язык: Английский
Процитировано
0