4.8 Article

Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization

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。
Review Chemistry, Multidisciplinary

Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings

Masahiro Murakami et al.

Summary: This article reviews synthetic transformations involving the cleavage of a carbon-carbon bond of a four-membered ring from 2011 to 2019, with a particular focus on progress in catalytic reactions such as oxidative addition and beta-carbon elimination, as well as the increasing attention on beta-scission of radical intermediates. Additionally, Lewis acid-mediated and thermally induced ring-opening of cyclobutanone derivatives have garnered renewed interest, demonstrating the unique synthetic potentials of structurally strained four-membered ring compounds for constructing organic skeletons.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Bioorthogonal Reactions Utilizing Nitrones as Versatile Dipoles in Cycloaddition Reactions

Didier A. Bilodeau et al.

Summary: Bioorthogonal chemical reactions involving nitrones have been optimized for efficient incorporation of unnatural functionality into living systems, with fast reaction rates. These reactions provide versatile tools for probing biological systems and have potential applications in biology.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

C-H Activation and Cross-Coupling of Acyclic Aldonitrone

Jakub Brzeskiewicz et al.

Summary: The palladium-catalyzed activation of C(sp(2))-H bond in an easily E,Z-isomerizable aldonitrone with an ester group at the C terminus enabled its cross-coupling with various aryl and heteroaryl bromides to produce ketonitrones. The reactions exhibited high E selectivity and the use of sterically hindered carboxylic acid as an additive, along with a non-polar solvent like toluene, was crucial for achieving good yields of the cross-coupling products. The obtained ketonitrones were further shown to be useful in dipolar cycloaddition or nucleophilic addition reactions.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Cyclic Nitrones by Chemoselective Intramolecular Allylic Alkylation of Oximes

Tobias Sandmeier et al.

Summary: The study introduces the enantio- and chemoselective N-allylation of oximes, yielding cyclic nitrones and enantioenriched aliphatic allylic alcohols through intramolecular kinetic resolution. The method stands out for its ability to utilize E/Z-isomeric oxime mixtures convergently and high functional group tolerance, showcasing its synthetic utility with the formal synthesis of (+)-halichlorine.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)-H Arylation with a Transient Directing Group

Philip A. Provencher et al.

Summary: The study presents a Pd(II)-catalyzed synthetic approach for methylene-selective C(sp(3))-H arylation of ketones, utilizing glycine as a directing group and a 2-pyridone ligand for methylene selectivity. The reaction exhibits high selectivity for intramolecular methylene C(sp(3))-H arylation, allowing for sequential C(sp(3))-H functionalization.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Enantioselective Synthesis of Cα-Tetrasubstituted N-Hydroxyl-α-amino Nitriles via Cyanation of Ketonitrones Using Me2(CH2Cl)SiCN

Peng-Wei Xu et al.

Summary: This study describes an unprecedented catalytic enantioselective cyanation of ketonitrones using a bifunctional cyanating reagent, Me-2(CH2Cl)SiCN, leading to the synthesis of optically active N-hydroxyl-alpha-amino nitriles. The use of this reagent not only achieves high enantioselectivity but also allows for diversification reactions of the resulting silylated adducts. Additionally, this work highlights the potential of tetrasubstituted C.N bonds for asymmetric synthesis of N-hydroxy alpha-amino acids and other N-hydroxy tertiary amines.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Modular Synthesis of Stereodefined Benzocyclobutene Derivatives via Sequential Cu- and Pd-Catalysis

Fabien J. T. Talbot et al.

Summary: A new synthetic method has been developed in this study to efficiently and selectively synthesize densely functionalized BCBs compounds, which can also be extended to the synthesis of other organic derivatives. The results provide new ideas and technical support for the synthesis of BCB compounds with specific functions.

ACS CATALYSIS (2021)

Review Chemistry, Applied

Recent Advances in the Synthesis of Spiro-β-Lactams and Spiro-δ-Lactams

Nuno G. Alves et al.

Summary: Spirocyclic molecules, especially the spiro-lactams subclass, are highly valued for their complex three-dimensional features and structural rigidity, making them extensively explored for their bioactivity and utility in various scientific fields such as drug design and organic synthesis. Efforts have been made towards developing new synthetic strategies for spirocyclic lactams due to their broad potential, with significant advancements reported since 2015 in the synthesis of spiro-beta-lactams and spiro-delta-lactams.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Review Chemistry, Organic

Recent Advances in Benzocyclobutene Chemistry

Samabasivarao Kotha et al.

Summary: The review highlights the significance of benzocyclobutene in bioactive natural products and medicinal molecules, as well as its value as a synthon for polymer building. Various preparation methods and applications in constructing complex structural frameworks are discussed, with anticipation of new applications emerging in the field.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Site-Selective C-C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis

Jing-Hong Guo et al.

Summary: In this study, an unprecedented highly selective cleavage of C1-C8 bond with the insertion of alkynes was achieved by using a blocking strategy via Ni catalysis. This provides an efficient method for the synthesis of 1,8-disubstituted naphthalenes, with the potential for easy removal of the blocking group after the transformation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

A ring expansion strategy towards diverse azaheterocycles

Ruirui Li et al.

Summary: This study presents a novel ring expansion strategy involving the cross-dimerization of different strained rings through synergistic bimetallic catalysis, providing an efficient and scalable method for assembling diverse N-heterocycles. Preliminary mechanistic studies reveal that the C-C bond of strained ring ketones is cleaved by the Pd-0 species during the reaction.

NATURE CHEMISTRY (2021)

Article Chemistry, Organic

Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

Yihang Li et al.

Summary: A protocol for synthesizing alpha-alkynylnitrones from 1,3-enynes has been developed using MgH2 triggered hydromagnesiation. The resulting alpha-alkynylnitrones can serve as versatile precursors for constructing various nitrogen-containing compounds.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition

Jianyu Zhang et al.

Summary: The authors report a formal type-II [4+4] annulation approach that provides fully sp(2)-carbon embedded anti-Bredt bicyclo[5.3.1] skeletons through the Rh-catalyzed C1-C8 activation of benzocyclobutenones and their coupling with pedant dienamides. This approach allows for the synthesis of complex bicyclo[5.3.1] scaffolds with yields up to 89%, and further conversion to tetracycles via a serendipitously discovered cascade reaction.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C-H functionalization

Jun Chen et al.

Summary: A sequential enantioselective reduction/C-H functionalization method was developed for installing contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy involves practical enantioselective reduction of a ketone and diastereospecific iridium-catalyzed C-H silylation, with further transformations explored, including controllable regioselective ring-opening reactions. Additionally, this strategy has been utilized for the synthesis of three natural products.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

Seema Thakur et al.

Summary: Cycloadditions are considered important chemical reactions, with nitrones reacting with various substrates to generate diverse heterocyclic rings that have wide-ranging applications.

NEW JOURNAL OF CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Small rings in the bigger picture: ring expansion of three- and four-membered rings to access larger all-carbon cyclic systems

Bohdan Biletskyi et al.

Summary: In this review, the release of ring strain in cyclobutane and cyclopropane derivatives is highlighted as a way to rapidly increase molecular complexity. The state-of-the-art of ring expansions involving three- and four-membered cycles is discussed, with an emphasis on reaction types and mechanisms. Selected examples are used to illustrate the synthetic potential of this elegant synthetic tool.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Synthesis of aza-quaternary centers via Pictet-Spengler reactions of ketonitrones

Tessa Lynch-Colameta et al.

Summary: This study presents a simple method for synthesizing a variety of products containing aza-quaternary centers by activating ketonitrones. The reaction process is mild, fast, and high-yielding, suitable for a diverse range of substrates, including those with electron-deficient substituents. Additionally, a catalytic asymmetric version has been developed, achieving good levels of enantioselectivity for several ketonitrones.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Divergent Coupling of Benzocyclobutenones with Indoles via C-H and C-C Activations

Hong Lu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Synthesis and Transformations of Nitrones for Organic Synthesis

Shun-Ichi Murahashi et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization

Bojun Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Medicinal

Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors

Gee-Hong Kuo et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2018)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Functionalization for Construction of Quaternary Carbon Centers

Yang Li et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Multidisciplinary

First Total Syntheses of Tetracenomycins C and X

Shogo Sato et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Intermolecular Heck-Like Coupling of Cyclobutanone Oximes Initiated by Selective C-C Bond Cleavage

Binlin Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines

Tyler W. Reidl et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Oxidative Ring Opening of Benzocyclobutenone Oximes: Novel Access to Stable Nitrile Oxides

Hiroshi Takikawa et al.

CHEMISTRY LETTERS (2017)

Article Chemistry, Multidisciplinary

1-Substituted 2-Azaspiro[3.3]heptanes: Overlooked Motifs for Drug Discovery

Alexander A. Kirichok et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)-H Carbamoylation

David Dailler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Cardiac & Cardiovascular Systems

Ivabradine: Heart Failure and Beyond

Rahul Chaudhary et al.

JOURNAL OF CARDIOVASCULAR PHARMACOLOGY AND THERAPEUTICS (2016)

Review Chemistry, Organic

Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups

Zhengkai Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

Review Chemistry, Multidisciplinary

Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities

Erick M. Carreira et al.

CHEMICAL REVIEWS (2014)

Article Chemistry, Organic

Kinugasa reaction: an 'ugly duckling' of β-lactam chemistry

Sebastian Stecko et al.

TETRAHEDRON (2014)

Review Chemistry, Multidisciplinary

Beyond Directing Groups: Transition-Metal-Catalyzed C-H Activation of Simple Arenes

Nadine Kuhl et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C-H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones

Paula Alvarez-Bercedo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Synthesis of 3,4-Dihydroisoquinolines by a C(sp(3))-H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine

Manon Chaumontet et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Organic

Cycloadditions of 1,1-Disubstituted Benzocyclobutenes Obtained by C(sp3)-H Activation

Manon Chaumontet et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Review Chemistry, Multidisciplinary

Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study

Manon Chaumontet et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Review Chemistry, Multidisciplinary

Cyclobutarenes and related compounds

AK Sadana et al.

CHEMICAL REVIEWS (2003)