4.5 Article

B(C6F5)(3)-Catalyzed Aza-Friedel-Crafts Reaction of Indolizines with 2-Aryl-3H-indol-3-ones

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of naphthols and electron-rich phenols with 2-aryl-3H-indol-3-ones

Tao Ma et al.

Summary: The highly enantioselective aza-Friedel-Crafts reaction of cyclic-ketimines and naphthols/phenols has been achieved using a chiral phosphoric acid catalyst. Various chiral aminonaphthols with a quaternary stereocenter were obtained with high yields and excellent enantioselectivity. The synthetic utility of the obtained products was demonstrated through efficient transformations.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Chemistry, Organic

Organocatalyzed Enantioselective Aza-Morita-Baylis-Hillman Reaction of Cyclic Ketimine with α,β-Unsaturated γ-Butyrolactam

Xi-Xi Wu et al.

Summary: The study developed a challenging direct organocatalytic asymmetric aza-MBH reaction involving cyclic ketimines attached to a neutral functional group. α,β-unsaturated γ-butyrolactam was used as a rare nucleophile alkene in this reaction. The reactions provided enantiomerically enriched 2-alkenyl-2-phenyl-1,2-dihydro-3H-indol-3-ones with high alpha-selectivities, high enantioselectivities (up to 99% ee), and good yields (up to 80%).

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Asymmetric aza-Friedel-Crafts Reaction of Cyclic Ketimines with 5-Aminopyrazole Derivatives: Expedient Access to Pyrazole-Based C2-quaternary Indolin-3-Ones

Xiu-Xiu Qiao et al.

Summary: A chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of 5-aminopyrazole derivatives with cyclic ketimines attached to a neutral functional group is reported, giving high enantioselectivities and regioselectivities in the formation of pyrazole-based C2-quaternary indolin-3-ones. Gram-scale synthesis of the 5-aminopyrazole-based C2-quaternary indolin-3-ones was also achieved without a decrease in yield and enantioselectivity.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

Article Chemistry, Organic

B(C6F5)3-catalyzed β-C(sp3)-H alkylation of tertiary amines with 2-aryl-3H-indol-3-ones

Chang-Peng Zou et al.

Summary: The beta-C-H functionalization of tertiary amines was achieved via the B(C6F5)(3)-catalyzed borrowing hydrogen strategy, leading to the synthesis of 1,3-diamines containing the indolin-3-one moiety in high yields. A possible catalytic cycle was proposed to explain the reaction process. Notably, the beta-C-H alkylation of amines is external oxidant- and transition-metal-free, making it economically favorable for chemical synthesis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Chemistry, Organic

Catalytic asymmetric conjugate addition of indolizines to unsaturated ketones catalyzed by chiral-at-metal complexes

Cheng Huang et al.

Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Applied

Asymmetric Organocatalyzed Friedel-Crafts Reaction of Trihaloacetaldehydes and Phenols

David Svestka et al.

Summary: Here we report an asymmetric organocatalyzed method for the Friedel-Crafts reaction between activated phenols and trihaloacetaldehydes. A screening of 41 compounds identified a catalyst structure based on 3,5-dinitrobenzamide of 9-amino-epi-cinchonidine as the lead catalytic molecule. Under optimized conditions, the catalyst provided trihalohydroxyalkylated adducts in good yields and with high enantiomeric ratios. The reaction scope was determined on 29 entries and several follow-up transformations of the enantioenriched products were accomplished.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Organic

Acetic Acid-Catalyzed Regioselective C(sp2)-H Bond Functionalization of Indolizines: Concomitant Involvement of Synthetic and Theoretical Studies

Kishor D. Mane et al.

Summary: An atom economical and environmentally benign protocol has been developed for the regioselective C(sp2)-H bond functionalization of indolizines. The protocol utilizes acetic acid as a metal-free catalyst to produce a wide range of synthetically useful indolizine derivatives.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Reductive Opening of Oxetanes Catalyzed by Frustrated Lewis Pairs:Unexpected Aryl Migration via Neighboring Group Participation

Luning Tang et al.

Summary: B(C6F5)3 catalyzes the unusual doublereduction of oxetanes by hydrosilane with aryl migration via neighboring group participation. Control experiments suggest that the phenonium ion serves as the key intermediate. Minor modifications of this protocol also enable simple hydrosilylative opening of oxetanes.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Base-promoted [4+2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

You-Ya Zhang et al.

Summary: A base-promoted [4 + 2] annulation reaction was developed for the synthesis of multisubstituted 5,6-dihydroindolizines through the reaction of pyrrole-2-carbaldehyde derivatives with beta,gamma-unsaturated alpha-ketoesters. DBN was used as the base, and the reaction proceeded smoothly under mild conditions, providing the target products in moderate to high yields, and tolerating many useful functional groups.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Enantioselective synthesis of α-tetrasubstituted (3-indolizinyl) (diaryl)methanamines via chiral phosphoric acid catalysis

Jialing Zhong et al.

Summary: An enantioselective Friedel-Crafts reaction of cyclic alpha-diaryl N-acyl imines with indolizines catalyzed by a chiral spirocyclic phosphoric acid has been developed, leading to the synthesis of alpha-tetrasubstituted (3-indolizinyl) (diaryl)methanamines with high enantioselectivity under mild conditions.

RSC ADVANCES (2022)

Article Chemistry, Multidisciplinary

A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones

Jian-Xiong An et al.

Summary: A simple and novel solid-supported organocatalyst was developed for the asymmetric Mannich reaction, resulting in high yields and excellent stereoselectivities. The catalyst can be easily recovered and reused without significant loss of catalytic efficiency.

RSC ADVANCES (2022)

Article Chemistry, Organic

Asymmetric Synthesis of Bridged N-Heterocycles with Tertiary Carbon Center through Barbas Dienamine-Catalysis: Scope and Applications

Jyothi Yadav et al.

Summary: A direct aza-Diels-Alder reaction between 2-aryl-3H-indolin-3-ones and cyclic-enones has been developed to access chiral indolin-3-one fused polycyclic bridged compounds. The method involves proline-catalyzed Barbas-dienamine intermediate formation from various cyclic-enones and has shown exciting photophysical activities. The synthesized compounds selectively sense Pd2+ and Fe3+ ions through the fluorescence quenching switch-off mode.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel-Crafts Conjugate Addition of Indolizines

Qijian Ni et al.

Summary: The research has successfully developed an organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition method for adding indolizines to cyclopentenediones to obtain the desired products. The utility of the method was demonstrated through various late-stage functionalizations.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Switching Chemoselectivity Based on the Ring Size: How to Make Ring-Fused Indoles Using Transition-Metal-Mediated Cross-Coupling

Jang-Yeop Kim et al.

Summary: Pd(0) and Cu(I) catalysts show distinct and complementary selectivities for the ring size of cyclic vinyl triflates. Pd(0) is effective for smaller rings while Cu(I) is effective for larger rings. This selectivity is attributed to differences in the bottlenecks of reductive elimination for Pd and oxidative addition for Cu, as well as bond strengths and transition state characteristics.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Tetracoordinate Boron Intermediates Enable Unconventional Transformations

Kai Yang et al.

Summary: Organoboron compounds are versatile reagents for building carbon-carbon and carbon-heteroatom bonds through tetracoordinate boron intermediates. Recent advances in improving tetracoordinate boron intermediates have been made, but challenges such as limited activation modes and difficulties in stereoselective control remain. New strategies involve constructing C-B bonds, C-C bonds, and designing and applying chiral tetracoordinate boron complexes.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Article Chemistry, Organic

Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives

Jiamin Lu et al.

Summary: The highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols was achieved by combining a chiral iridium complex catalyst with Lewis acid under mild conditions, delivering enantioenriched products in high yields and excellent selectivities. This protocol stands out for its availability of starting materials, mild conditions, broad substrate scope, high yields, excellent selectivity, and easy scalability, providing an efficient approach for the synthesis of chiral indolizines.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Aza-Diels-Alder Reaction of Ketimines and Unactivated Dienes

Qun Zhao et al.

Summary: The highly enantioselective aza-Diels-Alder reaction of 2-aryl-3H-indol-3-ones with unactivated dienes using a B(C6F5)(3)/chiral phosphoric acid catalyst system under mild conditions offers rapid access to a broad scope of tetrahydropyridine derivatives with excellent outcomes. The reaction is efficient, with maintained enantioselectivity even at lower catalyst loadings of 0.1 mol %. DFT calculations provide convincing evidence for the interpretation of stereoselection.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Metal-Free Catalyzed Synthesis of Fluorescent Indolizine Derivatives

Yu-Chang Yuan et al.

Summary: A mild and efficient method for the synthesis of indolizines using acid as a catalyst in a two-component reaction was developed. The reaction efficiently forms a new ring in one-step, yielding products in a range of 8-95% under metal-free conditions. Substituted indolizine derivatives were synthesized, with compound 3a yielding the best results at 95% and 82% under general and microwave irradiation conditions, respectively. Spectral analysis confirmed the structures of the synthesized compounds, with compound 3m further characterized by single crystal X-ray analysis. UV-vis absorption and fluorescence properties were correlated with substituent groups on the indolizine rings.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

Shyam Basak et al.

Summary: Boranes have the ability to mediate hydride abstraction from amino C-H bonds, resulting in the generation of reactive iminium hydridoborate salts that can participate in various stoichiometric and catalytic processes. These reactions include manipulation of amino scaffolds and the use of amine-based reagents for reactions such as transfer hydrogenation and alkylation.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Organic

Tris(pentafluorophenyl)borane catalyzed C-C and C-heteroatom bond formation

Gautam Kumar et al.

Summary: Tris(pentafluorophenyl)borane (BCF) has gained significant attention in the synthetic chemistry community as a potential Lewis acid catalyst due to its thermal stability and commercial availability. Recent research has focused on exploring BCF's role in metal-free catalysis, with many new catalytic reactivities under investigation. The review mainly categorizes different types of organic transformations mediated through BCF catalysis for the formation of C-C and C-heteroatom bonds.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Electron-deficient boron-based catalysts for C-H bond functionalisation

Yuanhong Ma et al.

Summary: Boron-based catalytic systems have shown great potential in C-H functionalization, enriching the chemistry field and providing opportunities in synthetic chemistry, materials chemistry, and chemical biology.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

B(C6F5)3/Chiral Phosphoric Acid Catalyzed Ketimine-Ene Reaction of 2-Aryl-3H-indol-3-ones and α-Methylstyrenes

Qing-Xia Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Catalyst-Free Conjugate Addition of Indolizines to In Situ-Generated Oxidized Morita-Baylis-Hillman Adducts

Thiago S. Silva et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality

Xi Yuan et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Organic

Bronsted-acid-catalyzed selective Friedel-Crafts monoalkylation of isatins with indolizines in water

Bruno Boni Guidotti et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Organic

Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives

Yi-Zhu Zhang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Organic

C-H Activation/Metalation Approaches for the Synthesis of Indolizine Derivatives

Camila R. de S. Bertallo et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Copper-Catalyzed Asymmetric Propargylation of Indolizines

Lei Yang et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Chemoselective Borane-Catalyzed Hydroarylation of 1,3-Dienes with Phenols

Guoqiang Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Rhodium(II)-Catalyzed Highly Stereoselective C3 Functionalization of Indolizines with N-Sulfonyl-1,2,3-triazoles

Nilesh Machhindra Kahar et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Visible light-mediated chemistry of indoles and related heterocycles

Alexey A. Festa et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Inorganic & Nuclear

Catalytic Hydroarylation of Alkenes with Phenols using B(C6F5)(3)

Jordan N. Bentley et al.

ORGANOMETALLICS (2018)

Review Chemistry, Multidisciplinary

Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free Hydrogenations and Hydrosilylations

Wei Meng et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Multidisciplinary

B(C6F5)3-Catalyzed C-Si/Si-H Cross-Metathesis of Hydrosilanes

Yuanhong Ma et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

B(C6F5)3-Catalyzed Michael Reactions: Aromatic C-H as Nucleophiles

Wu Li et al.

ORGANIC LETTERS (2017)

Article Chemistry, Organic

Total Synthesis of (±)-Grandilodine B

Chunyu Wang et al.

ORGANIC LETTERS (2017)

Article Chemistry, Multidisciplinary

B(C6F5)3-Promoted hydrogenations of N-heterocycles with ammonia borane

Fangwei Ding et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Alkylation Using Alkenes

Zhe Dong et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones

Jose Tiago Menezes Correia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Medicinal

Discovery and Characterization of GSK2801, a Selective Chemical Probe for the Bromodomains BAZ2A and BAZ2B

Peiling Chen et al.

JOURNAL OF MEDICINAL CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles

Masahiro Kojima et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

Alexander F. G. Maier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Mechanism of Boron-Catalyzed N-Alkylation of Amines with Carboxylic Acids

Qi Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Organic

Recent advances in the synthesis of indolizines and their pi-expanded analogues

Bartlomiej Sadowski et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Chemistry, Physical

B(C6F5)3-Catalyzed Reductive Amination using Hydrosilanes

Valerio Fasano et al.

ACS CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids

Ming-Chen Fu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pair Chemistry: Development and Perspectives

Douglas W. Stephan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

A unified survey of Si-H and H-H bond activation catalysed by electron-deficient boranes

Martin Oestreich et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pairs

Douglas W. Stephan

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

C3 functionalization of indolizines via In(III)-catalyzed three-component reaction

Youngeun Jung et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

Review Chemistry, Multidisciplinary

Frustrated Lewis Pairs: From Concept to Catalysis

Douglas W. Stephan

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Article Plant Sciences

Indole Alkaloid Glycosides from the Aerial Parts of Strobilanthes cusia

Wei Gu et al.

JOURNAL OF NATURAL PRODUCTS (2014)

Review Chemistry, Medicinal

Indolizine: a biologically active moiety

Vikas Sharma et al.

MEDICINAL CHEMISTRY RESEARCH (2014)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pair Catalyzed Hydroamination of Terminal Alkynes

Tayseer Mahdi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Enantioselective aza-Henry reactions of cyclic α-carbonyl ketimines under bifunctional catalysis

Alejandro Parra et al.

CHEMICAL COMMUNICATIONS (2012)

Review Chemistry, Multidisciplinary

Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones

Renato Dalpozzo et al.

CHEMICAL SOCIETY REVIEWS (2012)

Review Chemistry, Medicinal

Recent progress in synthesis and bioactivity studies of indolizines

Girija S. Singh et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Total Synthesis of (±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine

Xiangbing Qi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Inorganic & Nuclear

Luminescent CaWO4:Tb3+-Loaded Mesoporous Silica Composites for the Immobilization and Release of Lysozyme

Shanshan Huang et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2010)

Article Chemistry, Medicinal

Indole- and indolizine-glyoxylamides displaying cytotoxicity against multidrug resistant cancer cell lines

David A. James et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2008)

Review Chemistry, Multidisciplinary

Catalytic asymmetric Friedel-Crafts alkylation reactions-copper showed the way

Thomas B. Poulsen et al.

CHEMICAL REVIEWS (2008)

Article Chemistry, Medicinal

Discovery of protein-protein binding disruptors using multi-component condensations small molecules

Karim Bedjeguelal et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2006)

Article Chemistry, Medicinal

3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors

T Weide et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2006)

Article Chemistry, Organic

Palladium-catalyzed arylation and heteroarylation of indolizines

CH Park et al.

ORGANIC LETTERS (2004)

Review Chemistry, Multidisciplinary

New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction

M Bandini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Article Chemistry, Multidisciplinary

Reverse prenyl transferases exhibit poor facial discrimination in the biosynthesis of paraherquamide A, brevianamide A, and austamide

EM Stocking et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)