☆ 4.4 Review

Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Organic

Atmosphere- and Solvent-Controlled Coupling and Acetylation of Phenols Induced by Visible Light

Jiangtao Meng et al.

Summary: Tunable coupling or acetylation of phenol derivatives with diacetyl was achieved by switching the atmosphere and solvent induced by visible light without metal catalyst. Symmetric and asymmetric diphenols or binaphthols were obtained under aerobic conditions in water or 1,1,1,3,3,3-hexafluoroisopropanol, while phenol acetates were formed under argon in the presence of diacetyl and acetic acid. The ability to control chemo- and regioselectivities enhances the synthetic versatility of photoreactions.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Driven Photocatalyst-Free Deoxygenative Radical Transformation of Alcohols to Oxime Ethers

Wen-Hui Bao et al.

Summary: A visible-light-driven deoxygenative cross-coupling reaction of alcohols with sulfonyl oxime ethers has been developed using xanthate salts as alcohol-activating reagents. By convenient generation and direct photoexcitation of xanthate anions, a broad range of alcohols, including primary ones, can efficiently undergo this transformation to yield diverse oxime ethers and derivatives. This one-pot protocol offers mild conditions, broad substrate scope, and late-stage applicability without the need for external photocatalysts or electron donor-acceptor complex formation.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Physical

Photocatalytic One-Pot Synthesis of Quinazolinone Under Ambient Conditions

Mingchun Wang et al.

Summary: A novel photocatalytic cyclization reaction using 9-fluorenone as the photocatalyst has been developed for the synthesis of quinazolinones from o-aminobenzamides and in-situ generated aldehydes from alcohols. Furthermore, alcohols are found to be suitable alternatives to aldehydes due to their green, less toxic, available, and economical nature. The protocol showed good tolerance for various substrates and achieved high yields (up to 91%) of quinazolinones under ambient conditions.

CATALYSIS LETTERS (2023)

添加到收藏夹

Article Chemistry, Physical

Direct C-C Bond Formation of Allylic Alcohols with CO2 toward Carboxylic Acids by Photoredox/Nickel Dual Catalysis

Zhengning Fan et al.

Summary: The carboxylation reaction of allylic alcohols with carbon dioxide is achieved using photoredox/nickel dual catalysis, resulting in exclusively linear acids with good Z/E stereoselectivity. The use of Hantzsch ester as a reductant instead of stoichiometric metallic reductants allows the reaction to be carried out at room temperature with a blue LED light source. Mechanistic studies indicate that the presence of water in the catalytic system is crucial for the success of the reaction, which is likely to proceed through the oxidative addition of the in situ formed allylic hydrogen carbonate.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Physical

Visible-Light Photoredox-Catalyzed Carboxylation of Activated C(sp3)-O Bonds with CO2

Chuan-Kun Ran et al.

Summary: The study presents a visible-light photoredox-catalyzed carboxylation method that successfully synthesizes valuable aryl acetic acids under mild conditions without transition-metal catalysts. The method shows a broad substrate scope, good functional group tolerance, and can be applied to the synthesis of aliphatic carboxylic acids.

ACS CATALYSIS (2022)

添加到收藏夹

Review Chemistry, Organic

Radical Deoxyfunctionalisation Strategies

Khadijah Anwar et al.

Summary: Due to their abundance and ease of synthesis, alcohols are ideal for the selective derivatisation of organic molecules. Radical chemistry offers versatile strategies for the conversion of alcohols into various bonds, overcoming steric limitations associated with nucleophilic substitution pathways.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Boryl Radical Activation of Benzylic C-OH Bond: Cross-Electrophile Coupling of Free Alcohols and CO2 via Photoredox Catalysis

Wen-Duo Li et al.

Summary: A new strategy for direct cleavage of the C(sp3)-OH bond has been developed using neutral diphenyl boryl radical to activate free alcohols. Under mild visible light photoredox conditions, this strategy has been verified by cross-electrophile coupling of free alcohols and carbon dioxide to synthesize carboxylic acids. Control experiments and computational studies have shown that the activation of alcohols with neutral boryl radical leads to homolysis of the C(sp3)-OH bond, generating alkyl radicals, which can be further transformed into carbon anions for carboxylation with CO2 to form the coupling product.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)-C(sp3) Cross-Coupling via Radical Sorting

Holt A. Sakai et al.

Summary: Alcohols and carboxylic acids are important functional groups in organic chemistry that can undergo radical activation and transition metal catalysis under visible light photoredox catalysis. In this report, a dual combination of NHC-mediated deoxygenation and hypervalent iodine-mediated decarboxylation is used to achieve the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids. This method offers a mild and practical approach for the synthesis of alkyl-alkyl cross-coupled products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Organic

Direct Photoexcitation of Xanthate Anions for Deoxygenative Alkenylation of Alcohols

Hong-Mei Guo et al.

Summary: In this report, xanthate salts are identified as a unique class of visible-light-excitable alkyl radical precursors that serve as strong photoreductants and alkyl radical sources. Efficient deoxygenative alkenylation and alkylation of a wide range of primary, secondary, and tertiary alcohols have been achieved via direct photoexcitation of xanthate anions, without the need for photocatalysts. This method demonstrates a broad substrate scope and good functional group tolerance, allowing for late-stage functionalization of complex molecules.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation

Johnny Z. Wang et al.

Summary: In this paper, a convenient catalytic method for the coupling of alcohols with alkenes under mild photocatalytic conditions using N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition is described. This method is applicable to a wide range of alcohol compounds and allows for late-stage diversification reactions, showing significant potential for various applications.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Deoxytrifluoromethylation of Alcohols

Nicholas E. Intermaggio et al.

Summary: Deoxy-functionalization of alcohols is an important reaction in modern medicine. Deoxyfluorination is commonly used to introduce valuable fluorine atoms into drug-like molecules. However, there is currently no general method for deoxygenative trifluoromethylation of alcohols. This study presents a copper metallaphotoredox-mediated direct deoxytrifluoromethylation method.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Site-Selective Pyridine C-H Alkylation with Alcohols and Thiols via Single-Electron Transfer of Frustrated Lewis Pairs

Chang-Yin Tan et al.

Summary: A unified strategy for the deoxygenative or desulfurative pyridylation of various alcohols and thiols has been developed using a single-electron transfer (SET) process mediated by frustrated Lewis pairs (FLPs). The method involves the formation of FLPs between pyridinium salts and PtBu3, and the generation of alkyl radicals through the ionic coupling of phosphine radical cations with in situ generated xanthates. Visible-light irradiation enhances the reaction efficiency. This method offers a previously unrecognized opportunity for the selective heteroarylation of alcohols and thiols with diverse functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible-light-driven photocatalyst-free deoxygenative alkylation of imines with alcohols

Wei Zhang et al.

Summary: In this study, a photocatalyst-free visible-light-promoted deoxygenative alkylation method has been developed. Carbon disulfide and tricyclohexylphosphine are utilized to assist the activation of alcohols under the influence of visible light. This method allows for the selective bond cleavage of diverse primary, secondary, and tertiary alcohols via C-O homolysis, enabling their reaction with N-sulfonyl and N-aryl imines and providing a general and efficient platform for the synthesis of alpha-branched amines.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions

Zongbo Xie et al.

Summary: A facile tandem route has been developed for constructing quinazolinones using visible light without the need for additional photocatalysts. The use of alcohols as alternatives to aldehydes provides environmental, economic, stable, and low toxicity benefits, while also effectively reducing material loss.

CHINESE CHEMICAL LETTERS (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Metallaphotoredox-enabled deoxygenative arylation of alcohols

Zhe Dong et al.

Summary: Metal-catalysed cross-couplings are widely used for the formation of C-C bonds, but alkyl cross-couplings using alcohols as coupling partners remain relatively underdeveloped. A new method for direct deoxygenative cross-coupling of free alcohols has been developed, showing potential for a wide range of applications, including the pharmaceutical industry. This technology represents a general strategy for combining in situ alcohol activation with transition metal catalysis.

NATURE (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations

Hong-Mei Guo et al.

Summary: This study presents a novel strategy for deoxygenation of alcohols with electron-deficient alkenes through visible-light photoredox catalysis, efficiently generating various alkyl radicals including methyl radical and achieving selective monodeoxygenation of diols.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Induced Preparation of Quinazolinones by Oxidation of Benzyl Alcohols in Water

Fan Zhang et al.

Summary: A novel visible-light-induced reaction for the construction of quinazolinone derivatives via radical cyclization of 2-aminobenzamides with benzyl alcohols under water phase has been developed. It achieved high yields under mild conditions using I-2 as a photocatalyst, which is cheap, available and easy to handle. This method could provide a promising protocol for the synthesis of quinazolinone derivatives.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Catalyst-free reductive hydrogenation or deuteration of aryl-heteroatom bonds induced by light

Boyu Yan et al.

Summary: The study presents a simple and catalyst-free photochemical strategy for the direct reduction of aryl salts and haloarenes to arenes or deuterium-labeled arenes, confirming the formation of aryl radical intermediates.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Persistent Radical Effect in Organic Synthesis

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Transformation of Arenols Based on C-O Activation

Feng Liu et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Light-Driven Metal-Free Direct Deoxygenation of Alcohols under Mild Conditions

Dawei Cao et al.

ISCIENCE (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Transformations of Less-Activated Phenols and Phenol Derivatives via C-O Cleavage

Zihang Qiu et al.

CHEMICAL REVIEWS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Shining Light on C-S Bonds: Recent Advances in C-C Bond Formation Reactions via C-S Bond Cleavage under Photoredox Catalysis

Jian Gao et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

添加到收藏夹

Article Chemistry, Organic

Thiourea-Mediated Halogenation of Alcohols

Amar R. Mohite et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Organic

Metal-Free Deoxygenation of α-Hydroxy Carbonyl Compounds and Beyond

Maeva M. Pichon et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

添加到收藏夹

Review Chemistry, Organic

Recent Advance in the Transition-Metal Free Coupling Reactions for the Construction of C-X Bonds Induced by Light

Linjing Ren et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Transition Metal Catalyzed Deoxydehydration of Alcohols

Li Cui et al.

ACTA CHIMICA SINICA (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Spin-Center Shift-Enabled Direct Enantioselective alpha-Benzylation of Aldehydes with Alcohols

Eric D. Nacsa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photochemical activation of SF6 by N-heterocyclic carbenes to provide a deoxyfluorinating reagent

Pooja Tomar et al.

CHEMICAL COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Physical

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage Independent Activation of Strong C-O Bonds

Erin E. Stache et al.

ACS CATALYSIS (2018)

添加到收藏夹

Article Chemistry, Physical

Visible-Light-Driven Conversion of Alcohols into Iodide Derivatives with Iodoform

Yubao Zhao et al.

CHEMPHOTOCHEM (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Wenbo Liu et al.

CHEM (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

Yuki Takada et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Review Chemistry, Organic

Metal catalyzed defunctionalization reactions

Atanu Modak et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

添加到收藏夹

Review Chemistry, Organic

Recent Progress in Re-Catalyzed Dehydroxylation Reactions

Guoliang Mao et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2015)

添加到收藏夹

Article Multidisciplinary Sciences

Alcohols as alkylating agents in heteroarene C-H functionalization

Jian Jin et al.

NATURE (2015)

添加到收藏夹

Article Chemistry, Organic

Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst

Terry McCallum et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Organic

Photocatalytic Synthesis of Glycosyl Bromides

Xiaolong Yuan et al.

SYNTHESIS-STUTTGART (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Batch to flow deoxygenation using visible light photoredox catalysis

John D. Nguyen et al.

CHEMICAL COMMUNICATIONS (2013)

添加到收藏夹

Review Chemistry, Organic

Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton-McCombie Deoxygenation

Josef M. Herrmann et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

One-step selective deoxygenation of alcohols from acyloins

Jorge G. Uranga et al.

RSC ADVANCES (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Methylation Effect in Medicinal Chemistry

Eliezer J. Barreiro et al.

CHEMICAL REVIEWS (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible-light-mediated conversion of alcohols to halides

Chunhui Dai et al.

NATURE CHEMISTRY (2011)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.