eEtherification: An Electrochemical Strategy toward the Synthesis of Sterically Hindered Dialkyl Ethers from Activated Alcohols DOI
Cyrille Kiaku, Simon Kaltenberger, Daniel Raydan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Traditional etherification methods, although staples in synthetic chemistry, often fall short the efficient construction of sterically hindered dialkyl ethers, especially under mild and practical conditions. Recent advances have attempted to address these limitations, typically relying on transition metal catalysts, external reductants, or harsh reaction In this work, we disclose a novel electrochemical approach that enables synthesis ethers from economically relevant readily accessible alcohols without need for sacrificial oxidants. Our protocol exploits conditions generate reactive carbocations, which are subsequently captured by alcohol nucleophiles yield desired ethers. This method is cost-effective, practical, broad scope, providing valuable addition chemists' toolkit ether synthesis.

Language: Английский

C(sp3)–heteroatom bond formation by iron-catalyzed soft couplings DOI Creative Commons
Julius Semenya,

Yuan-Jie Yang,

Hye Joon Lee

et al.

Communications Chemistry, Journal Year: 2025, Volume and Issue: 8(1)

Published: March 8, 2025

Carbon–heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use metal-catalyzed cross-coupling reactions between sp2-hybridized organohalides soft heteroatomic nucleophiles for carbon–heteroatom bond formation, sp3-hybridized remain limited coupling with thiols remains elusive. Here, we report benzyl or tertiary halides thiol catalyzed by iron extend utility alcohol amine nucleophiles. The reaction is broad substrate scope both partners applicable construction congested tri- tetrasubstituted carbon centers as well β-quaternary synthetic further emphasized gram-scale synthesis rapid herbicide library synthesis. Overall, provide an efficient method prepare pharmaceutically materially relevant expanding iron-catalyzed organic chemistry, however, approaches access substrates limited. authors thiol,

Language: Английский

Citations

1
Electrochemical umpolung of C‐H nucleophiles bearing three electron‐withdrawing groups to trigger radical 1,2‐alkylarylations of allylic alcohols DOI Open Access
Qibin Li, Die Hu, Kun Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Abstract The electrochemical catalyst‐free generation of carbon radicals bearing three electron‐withdrawing groups from the corresponding C−H nucleophiles remains unexplored. To this end, we report a direct electro‐oxidation strategy to access these electrophilic under conditions. Enabled by strategy, radical 1,2‐alkylarylations allylic alcohols was realized, affording β ‐quaternary ketones with high functional group compatibility. This protocol is operationally simple and also easy scale up.

Language: Английский

Citations

0
Photocatalytic Germylation via Direct Hydrogen Atom Transfer DOI

Wenshan Wang,

Yan Liu,

Qiang Gao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Comprehensive Summary An innovative visible‐light‐driven direct hydrogen atom transfer ( d ‐HAT) of Ge–H bond has been developed, wherein the photoexcited 9,10‐phenanthraquinone PC HAT 9 ) serves as an efficient photocatalyst for generation germanium‐centered radicals from germanium hydrides including Ph 3 GeH, n Bu and 2 GeH . By employing hypervalent iodine reagents SOMOphiles, this protocol facilitates streamlined germylation through a mechanism involving germyl radical addition followed by β‐cleavage carboxyl to yield diverse array ethynyl‐, vinyl‐, nitrile‐, phenyl‐functionalized germanes. The methodological leap signifies noteworthy departure previous photocatalytic indirect i relying on combined usage SET with abstractors, which not only advances methodology creating in fashion but also provides access structurally novel pharmaceutically promising organogermanium compounds that are difficult synthesize routine methods.

Language: Английский

Citations

0
eEtherification: An Electrochemical Strategy toward the Synthesis of Sterically Hindered Dialkyl Ethers from Activated Alcohols DOI
Cyrille Kiaku, Simon Kaltenberger, Daniel Raydan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Traditional etherification methods, although staples in synthetic chemistry, often fall short the efficient construction of sterically hindered dialkyl ethers, especially under mild and practical conditions. Recent advances have attempted to address these limitations, typically relying on transition metal catalysts, external reductants, or harsh reaction In this work, we disclose a novel electrochemical approach that enables synthesis ethers from economically relevant readily accessible alcohols without need for sacrificial oxidants. Our protocol exploits conditions generate reactive carbocations, which are subsequently captured by alcohol nucleophiles yield desired ethers. This method is cost-effective, practical, broad scope, providing valuable addition chemists' toolkit ether synthesis.

Language: Английский

Citations

0