Three-Component Direct Phosphorylation of Aldehydes and Alkylation of Ketones: Synthesis of γ-Ketophosphine Oxides under Acidic Conditions

Article Chemistry, Organic

Synthesis of (Deoxy)difluoromethylated Phosphines by Reaction of R2P(O)H with TMSCF3 and Their Application in Cu(I) Clusters in Sonogashira Coupling

Xiaogang Yang et al.

Summary: R2PCF2H ligands and their precursors were synthesized by adjusting water concentration. These ligands can be stabilized in Cu(I) clusters and enable fast Sonogashira cross-coupling reaction at room temperature.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism

Zhaoliang Yang et al.

Summary: This study reports a method for the ring-opening functionalization of cycloalkanols using electrophotochemical catalysis. The method allows for selective cleavage of cycloalkanols with different ring sizes while tolerating various functional groups. The presence of chloride enables the selective formation of different types of bonds without the use of external oxidants.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Organic

Electrochemical Synthesis of β-Functionalized Ketones via Ring-Opening of Cycloalkanols

Lulu Zhao et al.

Summary: The electrochemical deconstructive functionalization of cycloalkanols with nucleophiles exclusively at the beta-position of ketones has been studied. A wide range of cycloalkanols and different N, O, C, and P-centered nucleophiles were used in this reaction, providing easy access to beta-functionalized ketones as products. The reaction involves the generation of alpha,beta-unsaturated ketones as key intermediates, followed by Michael addition with nucleophiles.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Hydrophosphorylation of electron-deficient alkenes and alkynes mediated by convergent paired electrolysis

Xue Sun et al.

Summary: This study presents a straightforward and practical strategy for hydrophosphorylation of electron-deficient alkenes and alkynes to access gamma-ketophosphine oxides. The strategy involves a convergent paired electrolysis (CPE) in the absence of a metal, base, and redox reagent. Mechanistic studies have revealed the dual role of diarylphosphane oxides as phosphorus radical precursors and hydrogen donors in this transformation.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Organic

Selective Catalytic Synthesis of α-Alkylated Ketones and β-Disubstituted Ketones via Acceptorless Dehydrogenative CrossCoupling of Alcohols

Dipanjan Bhattacharyya et al.

Summary: A phosphine-free pincer ruthenium(III) catalyzed beta-alkylation of secondary alcohols with primary alcohols to alpha-alkylated ketones and beta-branched ketones from two different secondary alcohols is reported. This environmentally friendly and atom efficient transformation produces only H2O and H-2 gas as byproducts. The protocol has been successfully scaled up to gram-scale reactions and applied to the functionalization of complex vitamin E and cholesterol derivatives.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Lewis Acid Enables Ketone Phosphorylation: Synthesis of Alkenyl Phosphonates

Xiao-Hong Wei et al.

Summary: An efficient method for synthesizing vinylphosphonates using ketones hydrophosphonylation has been developed with moderate to excellent yields, where water is the only byproduct in the reaction.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Applied

Synthesis of γ-Keto Sulfones through a Three-Component Reaction of Cyclopropanols, DABCO . (SO2)2 and Alkyl Halides

Chun Zhang et al.

Summary: A method for the synthesis of gamma-keto sulfones through a metal-free reaction involving cyclopropanols, DABCO, (SO2)2, and alkyl halides is described. The reaction proceeds efficiently under mild conditions in the absence of any catalysts, additives, or oxidants, with a good tolerance towards various functional groups. The proposed mechanism involves the formation of a gamma-keto sulfinate intermediate in situ, which then undergoes nucleophilic substitution with alkyl halides to yield gamma-keto sulfones.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Lewis Acid Enables Ketone Phosphorylation to Form a C-P Bond and a C-C Bond: Synthesis of 9-Phosphoryl Fluorene Derivatives

Xiao-Hong Wei et al.

Summary: An efficient method for the Lewis acid promotion of the synthesis of 9-phosphoryl fluorenes has been developed, focusing on ketone phosphonylation to form a C-P bond and a C-C bond between diphenylmethanone and H-phosphinate esters, H-phosphites, and H-phosphine oxides via phospha-aldol elimination. This method allows for the selective formation of a series of 9-phosphoryl fluorene derivatives in moderate to excellent yields.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Concise synthesis of N-phosphorylated amides through three-component reactions

Yuan-Yuan Zhu et al.

Summary: The study presented a novel strategy for the one-pot synthesis of N-phosphorylated amides via a three-component reaction. This is the first study to construct this framework through a multicomponent reaction, which is innovative, efficient, and cost-effective.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies

Aeysha Sultan et al.

MONATSHEFTE FUR CHEMIE (2020)

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Article Chemistry, Organic

Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Nina K. Gusarova et al.

SYNTHESIS-STUTTGART (2020)

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Article Chemistry, Organic

TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides

Runmin Zhao et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Carbene-Catalyzed Enantioselective Synthesis of γ-Keto-β-silyl Esters and Amides

Yuxia Zhang et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

A metal-free reaction of sulfur dioxide, cyclopropanols and electron-deficient olefins

Chun Zhang et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Organic

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles

Yi Li et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

The Silver-Promoted Phosphonation/Alkynylation of Alkene Proceeding with Radical 1,2-Alkynyl Migration

Shengnan Jin et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Three-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes

Xin-Gang Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Review Chemistry, Multidisciplinary

Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions

Qian Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Article Chemistry, Multidisciplinary

Hydrophosphorylation of Alkynes Catalyzed by Palladium: Generality and Mechanism

Tieqiao Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Organic

Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement

Yao Yin et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

1,4-Refunctionalization of β-diketones to γ-keto nitriles via C-C single bond cleavage

Qi Wu et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Article Chemistry, Organic

Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides

Changkai Shan et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Organic

Free-Radical-Promoted Copper-Catalyzed Decarboxylative Alkylation of α,β-Unsaturated Carboxylic Acids with ICH2CF3 and Its Analogues

Yan Zhu et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Organic

Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

Yulia A. Konik et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Article Chemistry, Organic

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

Luhao Lai et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Article Chemistry, Organic

Chemoselective Access to γ-Ketoesters with Stereogenic Quaternary α-Center or γ-Keto Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes

Song-Lin Zhang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Manganese-Catalyzed Hydrogen-Autotransfer C-C Bond Formation: α-Alkylation of Ketones with Primary Alcohols

Miguel Pena-Lopez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Photocatalytic C-C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex

Jing-Jing Guo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones

Guichun Fang et al.

CHEMISTRY-AN ASIAN JOURNAL (2016)

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Article Chemistry, Organic

PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes

Giacomo Strappaveccia et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

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Article Chemistry, Organic

Method for Direct Synthesis of α-Cyanomethyl-β-dicarbonyl Compounds with Acetonitrile and 1,3-Dicarbonyls

Chenyang Wang et al.

ORGANIC LETTERS (2016)

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Article Chemistry, Organic

Unactivated C(sp3)-H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies

Xing-Wang Lan et al.

ORGANIC LETTERS (2016)

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Article Chemistry, Multidisciplinary

Iron-Catalyzed α-Alkylation of Ketones with Alcohols

Saravanakumar Elangovan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Organic

Organocatalytic Enantioselective Direct Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactam to β-Acyl Acrylates and 1,2-Diacylethylenes

Yi-Ru Chen et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Phosphoric Acid-Catalyzed Asymmetric Classic Passerini Reaction

Jian Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ-Fluorinated Ketones

Huijun Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Palladium-catalysed norbornene-mediated C-H functionalization of arenes

Juntao Ye et al.

NATURE CHEMISTRY (2015)

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Article Chemistry, Organic

Catalyst- and Solvent-Free Rapid Addition of Secondary Phosphine Chalcogenides to Aldehydes: Another Click Chemistry

Nina K. Gusarova et al.

SYNTHESIS-STUTTGART (2015)

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Article Chemistry, Multidisciplinary

Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones

Qing Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration

Xue-Qiang Chu et al.

CHEMICAL COMMUNICATIONS (2014)

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Article Chemistry, Organic

N-Heterocyclic Carbene Catalyzed Carba-, Sulfa-, and Phospha-Michael Additions with NHC•CO2 Adducts as Precatalysts

Morgan Hans et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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Article Chemistry, Organic

Facile Synthesis of γ-Ketophosphonates by an Intermolecular Stetter Reaction onto Vinylphosphonates

Atanu Patra et al.

ORGANIC LETTERS (2014)

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Article Chemistry, Applied

N,N′-Dioxide-Scandium(III)-Catalyzed Asymmetric Michael Addition of β,γ-Unsaturated Butenolides to α,β-Unsaturated γ-Keto Esters

Jie Ji et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

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Article Chemistry, Organic

Bifunctional Titanocene Catalysis in Multicomponent Couplings: A Convergent Assembly of β-Alkynyl Ketones

Catherine A. Campos et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Multidisciplinary

Catalytic asymmetric construction of tetrasubstituted carbon stereocenters by conjugate addition of dialkyl phosphine oxides to β,β-disubstituted α,β-unsaturated carbonyl compounds

Depeng Zhao et al.

CHEMICAL COMMUNICATIONS (2012)

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Article Chemistry, Organic

Phospha-Michael Additions to Activated Internal Alkenes: Steric and Electronic Effects

Heather K. Lenker et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

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Article Chemistry, Organic

Enantioselective Synthesis of α-Stereogenic γ-Keto Esters via Formal Umpolung

G. K. Surya Prakash et al.

ORGANIC LETTERS (2012)

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Article Chemistry, Organic

Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated Aldehydes

Yun-Rong Chen et al.

ORGANIC LETTERS (2011)

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Article Chemistry, Multidisciplinary

Palladium(II)-catalyzed asymmetric hydrophosphination of enones: efficient access to chiral tertiary phosphines

Yinhua Huang et al.

CHEMICAL COMMUNICATIONS (2010)

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Article Chemistry, Organic

Zinc-Mediated Asymmetric Additions of Dialkylphosphine Oxides to α,β-Unsaturated Ketones and N-Sulfinylimines

Depeng Zhao et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Organic

Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

Pengfei Li et al.

ORGANIC LETTERS (2010)

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Article Chemistry, Organic

Efficient Synthesis of γ-Keto Esters through Neighboring Carbonyl Group-Assisted Regioselective Hydration of 3-Alkynoates

Weibo Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

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Article Chemistry, Organic

Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates

Steven C. Cullen et al.

ORGANIC LETTERS (2008)

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Article Chemistry, Multidisciplinary

A study on the Michael addition of dialkylphosphites to methylvinylketone

Gyorgy Keglevich et al.

HETEROATOM CHEMISTRY (2007)

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Review Chemistry, Multidisciplinary

Multi-component syntheses of heterocycles by transition-metal catalysis

Daniel M. D'Souza et al.

CHEMICAL SOCIETY REVIEWS (2007)

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Review Chemistry, Multidisciplinary

Fluorinated phosphonates: Synthesis and biomedical application

Vadim D. Romanenko et al.

CHEMICAL REVIEWS (2006)

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Article Chemistry, Multidisciplinary

Ir- and Ru-catalyzed sequential reactions: Asymmetric alpha-alkylative reduction of ketones with alcohols

Gen Onodera et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Article Chemistry, Multidisciplinary

Recyclable palladium catalyst for highly selective alpha alkylation of ketones with alcohols

MS Kwon et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Article Chemistry, Multidisciplinary

An efficient direct α-alkylation of ketones with primary alcohols catalyzed by [Ir(cod)Cl]2/PPh3/KOH system without solvent

K Taguchi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Organic

Tandem chain extension-homoenolate formation:: The formation of α-methylated-γ-keto esters

R Hilgenkamp et al.

ORGANIC LETTERS (2001)

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Article Chemistry, Multidisciplinary

Ruthenium-catalyzed propargylic alkylation of propargylic alcohols with ketones:: Straightforward synthesis of γ-keto acetylenes

Y Nishibayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

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Three-Component Direct Phosphorylation of Aldehydes and Alkylation of Ketones: Synthesis of γ-Ketophosphine Oxides under Acidic Conditions

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