Progress in the P(III)→P(V) Rearrangement Reaction of Phosphine Chlorides and Hydroxyl Containing Compounds DOI
Lulu Yang, Yi Cui, Jiale Wu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3639 - 3639

Published: Jan. 1, 2024

Language: Английский

Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis DOI
William Carson, Artem V. Tsymbal,

Robert W. Pipal

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(23), P. 15681 - 15687

Published: May 30, 2024

Alcohols are among the most abundant chemical feedstocks, yet they remain vastly underutilized as coupling partners in transition metal catalysis. Herein, we describe a copper metallaphotoredox manifold for open shell deoxygenative of alcohols with N-nucleophiles to forge C(sp3)–N bonds, linkage high value pharmaceutical agents that is challenging access via conventional cross-coupling techniques. N-heterocyclic carbene (NHC)-mediated conversion into corresponding alkyl radicals followed by copper-catalyzed C–N renders this platform successful broad range structurally unbiased and 18 classes N-nucleophiles.

Language: Английский

Citations

10
Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Couplings: Just a Change of the Reduction System? DOI

Wenhao Xu,

Tao Xu

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: 57(14), P. 1997 - 2011

Published: July 4, 2024

ConspectusIn recent years, nickel-catalyzed asymmetric coupling reactions have emerged as efficient methods for constructing chiral C(sp

Language: Английский

Citations

7
Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling DOI
Lulu Yang, Jiale Wu, Yang Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3208 - 3212

Published: April 10, 2024

Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms fragile C═N–O–PR2 species that undergoes N–O homolysis, fragmentation, and radical–radical coupling, leading to the formation cyano-containing phosphine oxides in good yields. The features an situ activation for radical generation, R2PCl plays dual role as both activator reactant.

Language: Английский

Citations

4
Development of an Easy-To-Handle Redox Active Group for Alcohols: Catalytic Transformation of Tertiary Alcohols to Nitriles DOI

Seung‐Hee Lee,

Gyumin Kang, Sunkyu Han

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5640 - 5645

Published: June 26, 2024

The generation of radical intermediates via SET-mediated deoxygenation activated alcohol derivatives is desirable, as alcohols can be utilized in various radical-mediated reactions. Herein, we introduce α-N-phthalimido-oxy isobutyrate (NPIB) a novel activating group for alcohols. Essentially, it more chemically robust alternative to Overman's N-phthalimidoyl oxalate group. utility the NPIB showcased conversion tertiary nitriles under Ir/Cu dual catalysts and presence TMSCN upon blue LED irradiation. With our newly developed handle, reactivities N-hydroxyphthalimide esters derived from carboxylic acids would achievable with naturally commercially abundant substrates.

Language: Английский

Citations

4
Metal- and Light-Free Decarboxylative Giese Addition Reaction Facilitated by Hantzsch Ester DOI
Lei Liang, X.Q. Deng, Hongbin Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 7, 2025

We have developed a novel strategy for decarboxylative radical addition reactions that employs ground-state reduced nicotinamide adenine dinucleotide (NADH) analogues under ambient and open-air conditions, facilitating the efficient formation of Csp3–Csp3 bonds in variety substrates. This protocol is distinguished by its operational simplicity, mild reaction high efficiency, use cost-effective starting materials. Furthermore, experimental studies provided valuable insights into mechanism, elucidating light-independent pathways promote these transformations.

Language: Английский

Citations

0
One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes DOI Creative Commons

Xiaojie Liu,

Biping Xu, Martin Oestreich

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 31, 2025

A formal deoxygenative silylation of primary alcohols is reported. The one-pot procedure consists an in situ bromination the alcohol and a subsequent nickel-catalyzed cross-electrophile coupling formed alkyl bromide various vinyl-substituted chlorosilanes. key to success compatibility nickel catalysis as well chlorosilane electrophile with byproducts preceding step, especially triphenylphosphine oxide likely acting weak ligand for excess catalyst used.

Language: Английский

Citations

0
Iron-Mediated One-Pot Dehydroxylative Cross-Electrophile Coupling of Alcohol with Disulfide for Thioether Synthesis by Using TCT as a Hydroxyl-Activating Agent DOI
Mengke Xu, X. Zhang, Yongqing Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

An efficient dehydroxythiolation between alcohols and disulfides using the widely abundant cheapest iron as a reaction mediator was developed. The one-pot thiolation proceeded effectively via C-O bond activation with aid of cyanuric chloride (TCT) hydroxyl-activating agent to give corresponding thioethers in modest excellent yields, displaying both wide substrate scope (applicable benzyl alcohol, allyl primary alkyl alcohol) good functional group tolerance. In addition, diselenide also proven be an appropriate for protocol, could subjected scale-up synthesis. Preliminary mechanistic examination revealed that transiently formed TCT-derived ether A, which is generated situ TCT possibly serves pivotal intermediate cross-electrophile thioetherification.

Language: Английский

Citations

0
Visible light-induced sulfonylation with sulfinates as closed-shell radical acceptors DOI
Dongyan Hu, L. Shen,

Su Su Htwe Chaw

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3497 - 3502

Published: Jan. 1, 2024

Sulfinates as close-shell radical acceptors instead of precursors for redox-neutral photochemical sulfonylation.

Language: Английский

Citations

2
Radical Deoxygenative Three-Component Reaction of Alcohols, Aryl Alkenes, and Cyanopyridines DOI

Li-Min Feng,

Shuai Liu,

Yuan‐Hong Tu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6225 - 6229

Published: July 15, 2024

We report herein a deoxygenative radical multicomponent reaction involving alcohols, aryl alkenes, and cyanopyridine under photoredox conditions. This method is photoredox-neutral, suitable for late-stage modification, compatible with wide array of alcohols as alkyl sources, including primary, secondary, tertiary alcohols. comprises relay mechanism encompassing the Giese addition alkenes by radicals, followed decyanative pyridination benzyl radicals.

Language: Английский

Citations

1
Photoinduced Deconstructive Alkylation Approach Enabled by Oxy-Radicals from Alcohols DOI

Yiman Gao,

Yan Li,

W. B. Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Alcohols are the most commercially abundant, synthetically versatile and operationally convenient functional groups in organic chemistry. Therefore, a strategy that utilizes hydroxy-containing compounds to develop novel bond disconnection formation process would achieve molecular diversity. Herein, deconstructive for generation of quinoxalin-2(1H)-one derivatives has been developed from alcohol precursors via oxy-radical-induced β-fragmentation. Additionally, 1,5-HAT deoxygenation by P(III) along with oxy-radical were demonstrated as alternative pathways this transformation. Furthermore, deep-seated reorganization few terpenes carbon framework, unique activity inhibition against growth pathogenic fungi was observed.

Language: Английский

Citations

0