TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines

Article Chemistry, Multidisciplinary

A Powerful Chiral Super Bronsted C-H Acid for Asymmetric Catalysis

Bingfei Peng et al.

Summary: By developing a new type of strong Bronsted C-H acids, the activity and enantioselectivity of catalytic reactions can be significantly improved, expanding the field of asymmetric Bronsted acid catalysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Physical

Perfluoroarene Interaction-Controlled Chiral Phosphoric Acid-Catalyzed Enantioselective Michael Addition of Difluoroenoxysilanes to Azadienes: a Combination of Experimental and Theoretical Studies

Jinshan Li et al.

Summary: A catalytic and highly enantioselective Mukaiyama-Michael addition of difluoroenoxysilanes to azadienes has been developed using perfluorinated aryl-incorporating chiral monophosphoric acid (PF-CPA) as an effective catalyst. The presence of perfluoroaryl substituents not only enhances catalytic activity but also creates a confined chiral environment for highly enantioselective transformations.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel-Crafts Reactions

Hongchen Li et al.

Summary: A novel tandem synthesis of 1,3-disubstituted naphthalenes is developed using TfOH-promoted directed-aldol and Friedel-Crafts reactions. The discovery of a chemoselective directed-aldol reaction between different ketones with alpha-hydrogens enables the efficient creation of new C-C bonds and a benzene ring in one pot.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Cascade Cyclization of Azadienes with Difluoroenoxysilanes: A One-Pot Formal [4+2] Approach to Fluorinated Polyfused Heterocycles

Jinshan Li et al.

Summary: A TfOH-promoted method for synthesizing fluorinated poly-fused heterocycles has been developed, allowing the convenient construction of fluorinated benzofuro[3,2-b]pyridines, 5H-indeno-[1,2-b]pyridines, and 5,6-dihydrobenzo[h]quinolines. This method involves a one-pot [4 + 2] approach and is highlighted by the successful synthesis of three fluoro analogues of bioactive molecules.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Chiral Phosphoric Acid-Catalyzed C6 Functionalization of 2,3-Disubstituted Indoles for Synthesis of Heterotriarylmethanes

Wen-Jun Huang et al.

Summary: The study presents a method for direct regio- and enantioselective C6 functionalization of 2,3-disubstituted indoles with azadienes using chiral phosphoric acid as catalyst. Mechanistic studies show that N-alkylation of 2,3-disubstituted indoles with azadienes is reversible, enabling enantioselective C6 functionalization.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

N-Heterocyclic Carbene-Catalyzed Formal [3+3] Annulation of Alkynyl Acylazoliums for the Synthesis of Benzofuro[3,2-b]pyridin-2-ones

Xiaoxue Wang et al.

Summary: Through N-heterocyclic carbene catalysis, a formal [3+3] annulation of alkynyl acylazoliums with indolin-3-ones has been developed for the rapid construction of benzofuro[3,2-b]pyridin-2-ones with potential bioactivities. This method offers a highly efficient and simple synthesis of target molecules under mild reaction conditions, with a wide substrate scope and excellent chemoselectivity, as well as versatile late-stage modifications.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Reversal of Regioselectivity in Nucleophilic Difluoroalkylation of α,β-Enones Employing In Situ-Formed Sterically Encumbered Silylium Catalyst

Jinshan Li et al.

Summary: An efficient method has been developed for the reversal of regioselectivity in the nucleophilic introduction of difluorinated carbanion into alpha, beta-enones via silylium catalysis. The strong electron-withdrawing properties and bulky substituents of in situ-generated silyl triflic imide catalyst play a key role in the successful 1,4-addition reaction. The synthetic utility of this method is demonstrated by its further application in the one-pot synthesis of 2,4,6-triarylsubstituted 3-fluoropyridines.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Iron-Catalyzed Highly Enantioselective Addition of Silyl Enol Ethers to α,β-Unsaturated 2-Acyl Imidazoles

Jinhu Wei et al.

Summary: The chiral Fe-II(N4) complex developed is an effective chiral Lewis acid for the asymmetric conjugate addition of silyl enol ethers to alpha,beta-unsaturated 2-acyl imidazoles, resulting in high yields and enantioselectivities (up to 99% ee) of chiral 1,5-dicarbonyl synthons and cyclohexenone derivatives.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Base-Catalyzed Sequential 1,4-Addition/Intramolecular Cyclization/Aromatization Reaction: Synthesis of Benzofuro[3,2-b]pyridines

Yimin Hu et al.

Summary: An efficient method using K2CO3 catalysis has been developed for the 1,4-addition/intramolecular cyclization/aromatization reaction of aurone-derived 1-azadienes with trisubstituted allenoates, resulting in a series of benzofuro[3,2-b]pyridines in moderate to excellent yields. The reaction proceeds efficiently under an air atmosphere without the need for transition metal catalysts, providing a concise approach to benzofuro[3,2-b]pyridines.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

Pei-Xue Gong et al.

Summary: A practical iron-catalyzed domino decarboxylation-oxidation reaction has been developed for the synthesis of methyl ketones from alpha,beta-unsaturated carboxylic acids. This method is mild, operationally simple, uses ambient air as the sole oxidant, and tolerates sensitive functional groups for late-stage functionalization of complex molecules.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Physical

Tandem synthesis of tetrahydroquinolines and identification of the reaction network by operando NMR

Jingwen Chen et al.

Summary: This study explored the reaction mechanism and complex network of heterogeneously catalyzed tandem reactions using bifunctional metal-organic framework supported Pd nanoparticles. The operando magic angle spinning nuclear magnetic resonance studies provided insights into intermediates and products evolution, helping to deduce the reaction network. The optimized procedure yielded valuable substituted tetrahydroquinolines, demonstrating new opportunities for efficient and sustainable synthesis of medicinally relevant building blocks.

CATALYSIS SCIENCE & TECHNOLOGY (2021)

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Article Chemistry, Multidisciplinary

Highly Regio-, Diastereo-, and Enantioselective Synthesis of Tetrahydroazepines and Benzo[b]oxepines through Palladium-Catalyzed [4+3] Cycloaddition Reactions

Barry M. Trost et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Control of Chemical Reactions by Using Molecules that Buffer Non-aqueous Solutions

Muhammad Sohail et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Review Chemistry, Multidisciplinary

Recent Advances in the Cycloaddition Reactions of 2-Benzylidene-1-benzofuran-3-ones, and Their Sulfur, Nitrogen and Methylene Analogues

Qingsong Deng et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

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Article Chemistry, Organic

Collaborative Activation of Trifluoroacetyl Diazoester by a Lewis Acid and Base for the Synthesis of Polysubstituted 4-Trifluoromethylpyrazoles

Zheng Fang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Organocatalytic 1,4-Addition of Azadienes with 3-Homoacyl Coumarins toward Highly Enantioenriched Benzofuran Coumarin Skeletons

Juzhang Yan et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Catalytic asymmetric 1,4-type Friedel-Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes

Cheng-Jie Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Article Chemistry, Applied

Potential hypoglycemic effect of acetophenones from the root bark of Cynanchum wilfordii

Hao-Wen Jiang et al.

NATURAL PRODUCT RESEARCH (2019)

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Article Chemistry, Organic

[4+1+1] Annulations of α-Bromo Carbonyls and 1-Azadienes toward Fused Benzoazaheterocycles

Rong Zeng et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

BINOL Phosphoric Acid-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Acyl Ketimines with Cyclic Enones

K. Nagarjuna Reddy et al.

CHEMISTRY-AN ASIAN JOURNAL (2019)

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Article Chemistry, Organic

Copper-Catalyzed Alkynylation/Cyclization/Isomerization Cascade for Synthesis of 1,2-Dihydrobenzofuro[3,2-b]pyridines and Benzofuro[3,2-b]pyridines

Huan-Ping Xie et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Applied

Organocatalytic Asymmetric Michael Addition of Rhodanines to Azadienes for Assembling of Sulfur-containing Tetrasubstituted Carbon Stereocenters

Wei Lin et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Organic

Organocatalytic enantioselective direct vinylogous Michael addition of γ-substituted deconjugate butenolides to azadienes

Wei Lin et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

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Article Chemistry, Organic

Reductive coupling of alkenes with unsaturated imines via a radical pathway

Jifeng Qi et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

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Article Chemistry, Organic

Catalytic Asymmetric Conjugate Addition of Tritylthiol to Azadienes with a Bifunctional Organocatalyst

Zheng Gu et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Synthesis of chiral γ-aminophosphonates through the organocatalytic hydrophosphonylation of azadienes with phosphites

Zheng Gu et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Article Chemistry, Applied

Synthesis of Indenopyridine Derivatives via MgI2-Promoted [2+4] Cycloaddition Reaction of In-situ Generated 2-Styrylmalonate from Donor-Acceptor Cyclopropanes and Chalconimines

Kamal Verma et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclic C-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones

Jin-Shan Li et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Organic

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Tomas Javorskis et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Branched-Selective Intermolecular Ketone α-Alkylation with Unactivated Alkenes via an Enamide Directing Strategy

Dong Xing et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Multidisciplinary

In situ formed acetals facilitated direct Michael addition of unactivated ketones

Srinivasa Rao Koppolu et al.

NEW JOURNAL OF CHEMISTRY (2017)

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Article Chemistry, Organic

Hexafluoroisopropanol-Promoted Metal-Free Allylation of Silyl Enol Ethers with Allylic Alcohols

Juana M. Perez et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/BrOnsted Base Complexes

Ming Shang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Medicinal

2-Chlorophenyl-substituted benzofuro[3,2-b] pyridines with enhanced topoisomerase inhibitory activity: The role of the chlorine substituent

Til Bahadur Thapa Magar et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2017)

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Article Chemistry, Multidisciplinary

Direct α-Alkylation of Acetophenones with Benzhydrols as Well as 1-Phenylethanols Using Amberlyst-15/Ionic Liquid as an Efficient Catalytic System

Kishor V. Wagh et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2016)

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Article Chemistry, Applied

Synthesis of Benzofurans from Ketones and 1,4-Benzoquinones

Fengtian Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

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Article Chemistry, Multidisciplinary

Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes

Bahria Touati et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

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Article Chemistry, Multidisciplinary

A Catalyst-Enabled Diastereodivergent Aza-Diels-Alder Reaction: Complementarity of N-Heterocyclic Carbenes and Chiral Amines

Zi-Qiang Rong et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

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Article Chemistry, Multidisciplinary

Asymmetric Mannich Reaction of Aryl Methyl Ketones with Cyclic Imines Benzo[e][1,2,3]oxathiazine 2,2-Dioxides Catalyzed by Cinchona Alkaloid-based Primary Amines

Xiao-Yu Cui et al.

CHEMISTRY-AN ASIAN JOURNAL (2016)

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Article Plant Sciences

Barrier protective effects of 2,4,6-trihydroxy-3-geranyl acetophenone on lipopolysaccharides-stimulated inflammatory responses in human umbilical vein endothelial cells

Yi Joong Chong et al.

JOURNAL OF ETHNOPHARMACOLOGY (2016)

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Article Chemistry, Applied

Silver Hexafluoroantimonate-Catalyzed Direct α-Alkylation of Unactivated Ketones

Naganaboina Naveen et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

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Article Chemistry, Medicinal

A Series of Novel Terpyridine-Skeleton Molecule Derivants Inhibit Tumor Growth and Metastasis by Targeting Topoisomerases

Han-Byeol Kwon et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Direct Asymmetric Amination of α-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid

Xiaoyu Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

In Situ Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from o-Alkenylbenzaldehydes

Seetharaman Manojveer et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Organic

Bifunctional Amino Sulfonohydrazide Catalyzed Direct Asymmetric Mannich Reaction of Cyclic Ketimines with Ketones: Highly Diastereo- and Enantioselective Construction of Quaternary Carbon Stereocenters

Sheng Zhang et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Organic

Triflic Acid Promoted Direct α-Alkylation of Unactivated Ketones Using Benzylic Alcohols via in Situ Formed Acetals

Srinivasa Rao Koppolu et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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Article Chemistry, Applied

Michael Addition of Ketones and Aldehydes to Maleimides Catalyzed by Modularly Designed Organocatalysts

Savitha Muramulla et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

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Article Chemistry, Multidisciplinary

2,4-Diaryl Benzofuro[3,2-b]pyridine Derivatives: Design, Synthesis, and Evaluation of Topoisomerase Inhibitory Activity and Cytotoxicity

Pritam Thapa et al.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2013)

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Article Chemistry, Organic

Theoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis

Chen Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

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Article Chemistry, Multidisciplinary

The Direct Asymmetric a Alkylation of Ketones by Bronsted Acid Catalysis

Liu Song et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Article Chemistry, Multidisciplinary

Organocatalytic Synthesis of 1,2,3-Triazoles from Unactivated Ketones and Arylazides

Mokhtaria Belkheira et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

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Article Chemistry, Organic

Chiral Bifunctional Thiourea-Catalyzed Enantioselective Michael Addition of Ketones to Nitrodienes

Hai Ma et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Organic

Development of the first Bronsted acid assisted enantioselective Bronsted acid catalyzed direct Mannich reaction

Magnus Rueping et al.

SYNLETT (2007)

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Article Chemistry, Multidisciplinary

Chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction

Qi-Xiang Guo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Multidisciplinary

A simple primary-tertiary diamine-Bronsted acid catalyst for asymmetric direct Aldol reactions of linear aliphatic ketones

Sanzhong Luo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Organic

Highly enantioselective michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides

Kun Liu et al.

ORGANIC LETTERS (2007)

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Article Chemistry, Organic

Microwave-assisted four-component, one-pot condensation reaction: an efficient synthesis of annulated pyridines

Chao-Guo Yan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2007)

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Article Chemistry, Multidisciplinary

Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes

Sunil V. Pansare et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Article Chemistry, Multidisciplinary

Anti-inflammatory effect of amurensin H on asthma-like reaction induced by allergen in sensitized mice

Yi-Tang Li et al.

ACTA PHARMACOLOGICA SINICA (2006)

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Article Chemistry, Medicinal

Synthesis and structure-affinity-activity relationships of novel benzofuran derivatives as MT2 melatonin receptor selective ligands

V Wallez et al.

JOURNAL OF MEDICINAL CHEMISTRY (2002)

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TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines

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