Ph3P/ICH2CH2I-promoted reductive deoxygenation of alcohols DOI

Wen-Huan Tang,

Xing Zheng,

Xu Yao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(45), P. 8989 - 8992

Published: Jan. 1, 2023

Owing to the ubiquity of hydroxyl group, reductive deoxygenation alcohols has become an active research area. The classic Barton-McCombie reaction suffers from a tedious two-step procedure. New efficient methods have been developed, but they some limitations, such as narrow substrate scope and use moisture-sensitive Lewis acids. In this work, we describe Ph3P/ICH2CH2I-promoted with NaBH4. process is applicable benzyl, allyl propargyl alcohols, also primary secondary demonstrating wide good level functional group tolerance. This protocol features convenient operation low cost all reagents.

Language: Английский

Photocatalytic reduction of fluoroalkyl-substituted alcohols activated by pentafluoropyridine DOI

Sergey S. Lunkov,

Artem A. Zemtsov,

Vitalij V. Levin

et al.

Mendeleev Communications, Journal Year: 2023, Volume and Issue: 33(3), P. 387 - 389

Published: May 1, 2023

Language: Английский

Citations

4
Direct Deoxygenative Homocoupling of Alcohols to Access C(sp3)–C(sp3) Bonds via Synergistic Ruthenium/Nickel Catalysis DOI
Dawei Cao, Shumei Xia, Lijuan Li

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(19), P. 14966 - 14973

Published: Sept. 25, 2024

Language: Английский

Citations

1
Ph3P═O-Catalyzed Reductive Deoxygenation of Alcohols DOI
Qiang Li, Yu Sun,

Mu-Xian Fu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 16022 - 16027

Published: Oct. 11, 2024

Reductive deoxygenation of alcohols is particularly challenging because the high bond dissociation energy C–OH and poor leaving ability hydroxyl group. Herein we describe a Ph3P═O-catalyzed reductive benzyl with PhSiH3 under an air atmosphere within 30 min reaction time. The use catalytic loading Ph3P═O enhances practicality this protocol.

Language: Английский

Citations

1
Electroreductive formylation of activated alcoholsviaradical–polar crossover DOI

Jung-Taek Kang,

Heyjin Cho,

Hyunwoo Kim

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(38), P. 5733 - 5736

Published: Jan. 1, 2023

The direct synthesis of sterically hindered aldehydes is highly challenging. Herein, we report a approach to generate such compounds via electroreductive cleavage the C(sp3)-O bond activated alcohols. Under established reaction conditions, benzylic radical intermediates were efficiently generated. A subsequent radical-polar crossover generated carbanions that further reacted with N,N-dimethylformamide form various tertiary or quaternary carbon centers. feasibility gram-scale was also demonstrated. This operated in simple undivided cell, which avoids use any transition metal catalysts, toxic gas, and reductants.

Language: Английский

Citations

2
Ph3P/ICH2CH2I-promoted reductive deoxygenation of alcohols DOI

Wen-Huan Tang,

Xing Zheng,

Xu Yao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(45), P. 8989 - 8992

Published: Jan. 1, 2023

Owing to the ubiquity of hydroxyl group, reductive deoxygenation alcohols has become an active research area. The classic Barton-McCombie reaction suffers from a tedious two-step procedure. New efficient methods have been developed, but they some limitations, such as narrow substrate scope and use moisture-sensitive Lewis acids. In this work, we describe Ph3P/ICH2CH2I-promoted with NaBH4. process is applicable benzyl, allyl propargyl alcohols, also primary secondary demonstrating wide good level functional group tolerance. This protocol features convenient operation low cost all reagents.

Language: Английский

Citations

2