4.7 Article

Pd-catalyzed regioselective rollover dual C-H annulation cascade: facile approach to phenanthrene derivatives

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

Palladium-Catalyzed [5+2] Rollover Annulation of 1-Benzylpyrazoles with Alkynes: A Direct Entry to Tricyclic 2-Benzazepines

Alejandro Suarez-Lustres et al.

Summary: The first Pd-catalyzed [5 + 2] rollover annulation of 1-benzylpyrazoles with alkynes has been developed to assemble 10H-benzo[e]pyrazolo-[1,5-a]azepines (tricyclic 2-benzazepines). The rollover annulation involves twofold C-H activation of aryl and heteroaryl C-sp(2)-H bonds (C-H/C-H) of 1-benzylpyrazoles (five-atom partners) and alkynes, resulting in [5 + 2] annulated compounds.

ORGANIC LETTERS (2023)

Article Chemistry, Applied

Rhodium-Catalyzed Dual C-H Activation for Regioselective Triple Annulation of Enaminones: Access to Polycyclic Naphthopyran Derivatives

Vavilapalli Suresh et al.

Summary: The Rh-catalyzed C-H activation of arenes for oxidative annulations with alkynes is an efficient method to form polycyclic scaffolds. In this study, a regioselective triple annulation of enaminones with hydroxyl-alkynoates via double C-H functionalization was achieved by rhodium catalysis, resulting in polycyclic naphtho-pyran scaffolds. The regioselectivity was controlled by the secondary coordination of hydroxyl group in alkynoate.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Article Multidisciplinary Sciences

Enantioselective electrochemical cobalt-catalyzed aryl C-H activation reactions

Tristan von Muenchow et al.

Summary: Enantioselective oxidation reactions typically rely on costly transition metals and stoichiometric amounts of chemical oxidants. This study demonstrates a sustainable alternative by using electrocatalysis, specifically the hydrogen evolution reaction (HER), in place of a chemical oxidant. The use of cobalt catalyst for asymmetric oxidation enables highly enantioselective aryl carbon-hydrogen bond (C-H) activation reactions, leading to the synthesis of chiral compounds. Additionally, cobalt-mediated electrocatalysis allows for selective desymmetrization through dehydrogenative C-H activation reactions, facilitating the preparation of sterically complex phosphorus (P)-stereogenic compounds.

SCIENCE (2023)

Article Chemistry, Multidisciplinary

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C-H Functionalization/Dual Oxidative Cyclization

Dattatri et al.

Summary: The C-H functionalization strategy simplifies the synthesis of valuable molecules. Using a single bifunctional reagent for dual C-H unsymmetrical functionalization is effective. Propargyl alcohols (PAs) have not been explored as building blocks via oxidative cleavage, but they can be used as new bifunctional reagents for regioselectively annulated outcomes of biphenylamine. This method allows for late-stage diversification of natural products.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Organic

Rhodium-Catalyzed Regioselective Double Annulation of Enaminones with Propargyl Alcohols: Rapid Access to Arylnapthalene Lignan Derivatives

Attunuri Nagireddy et al.

Summary: This research presents a rhodium-catalyzed oxidative three-point double annulation of enaminones with propargylic alcohols to access arylnaphthalene-based lignan derivatives. The key step involves the regioselective insertion of propargylic alcohol into the rhoda-cycle due to hydroxyl rhodium coordination, with mechanism determined through control experiments and KIE studies.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3+2] spiroannulations

Wen Wei et al.

Summary: This study demonstrates the synthesis of biologically relevant three-dimensional spirocyclic compounds through electrocatalysis, using palladium and rhodium(iii) catalysts, with electricity as a green oxidant. The spiroannulation reactions were successfully achieved with a wide substrate scope under mild conditions in an undivided cell setup, with molecular hydrogen as the sole byproduct.

CHEMICAL SCIENCE (2022)

Article Chemistry, Physical

Modern Palladium-Catalyzed Transformations Involving C-H Activation and Subsequent Annulation

Raju S. Thombal et al.

Summary: Metal catalyzed cascade C-H activation/annulation is a highly promising approach for the construction of aromatic and heteroaromatic compounds. Pd-complexes play a crucial role in this method, enabling high catalytic efficiency through the activation of molecules bearing a directing group.

ACS CATALYSIS (2022)

Article Chemistry, Organic

Rh(III)-Catalyzed Weakly Coordinating 2-Pyridone-Directed Oxidative Annulation Using Internal Alkynes: A Reversal in Selectivity

Satabdi Bera et al.

Summary: A rhodium(III)-catalyzed Satoh-Miura type oxidative annulation of N-aryl 2-pyridone derivatives using internal alkyne as a coupling partner is described. The weakly coordinating carbonyl group of the 2-pyridone ring is utilized for this transformation, allowing for a broad scope and wide functional group tolerance. The solvent plays an important role in providing a different class of annulated product. Preliminary investigation of the photophysical properties of the obtained polyarylated N-naphthyl 2-pyridones was also conducted.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Rhodium-Catalyzed Coordination-Assisted Regioselective and Migratory Three-Point Double Annulation of o-Alkenyl Phenols with Tertiary Propargyl Alcohols

Attunuri Nagireddy et al.

Summary: We have developed a new synthetic method for the selective construction of naphtho furan derivatives. This method enables the formation of two new rings and four new bonds in one reaction without the need for any additives. The mechanism of the reaction has been elucidated through labeled and control experiments, revealing the crucial role of a tertiary hydroxyl group in controlling the regioselective insertion of an alkyne and driving the ring expansion via selective olefin reshuffling. The scalable protocol also demonstrates tolerance for late stage functionalization of natural products.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Switching the Reactivity of the Nickel-Catalyzed Reaction of 2-Pyridones with Alkynes: Easy Access to Polyaryl/Polyalkyl Quinolinones

Namrata Prusty et al.

Summary: A Ni-catalyzed cascade reaction between 2-pyridone and alkynes has been achieved by tuning reaction conditions and incorporating a directing group. The use of sodium iodide as an additive plays a crucial role in the success of this transformation. The detection of a five-membered metallacycle intermediate through HRMS provides insights into the reaction mechanism.

ORGANIC LETTERS (2022)

Review Chemistry, Multidisciplinary

Recent Advances in Alkenyl sp2 C-H and C-F Bond Functionalizations: Scope, Mechanism, and Applications

Ming-Zhu Lu et al.

Summary: This comprehensive review provides an overview of the latest methods for selectively activating alkenyl C(sp2)-H and C-F bonds to access alkenes and their derivatives. It is divided into two parts, the first part focuses on C-H functionalization methods using different alkene derivatives as starting materials, and the second part describes C-F bond functionalization using easily accessible gem-difluoroalkenes. The review includes scope, limitations, mechanistic studies, stereoselective control, and applications in complex molecule synthesis.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

Phenanthrene[2]arene: synthesis and application as nonporous adaptive crystals in the separation of benzene from cyclohexane

Fei Zeng et al.

Summary: In this study, a new macrocycle, phenanthrene[2]arene, with nanometer-sized cavities, was designed and synthesized. The nonporous adaptive crystals of phenanthrene[2]arene showed excellent adsorption capacity for benzene (PhH) and were able to separate PhH from an equimolar mixture of PhH and cyclohexane (Cy) with high purity and under mild conditions. The system also demonstrated fast adsorption, high loading ratios, high purity, and easy recycling, making it promising for practical applications.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Phenanthrene[2]arene: synthesis and application as nonporous adaptive crystals in the separation of benzene from cyclohexane

Fei Zeng et al.

Summary: In this study, a new macrocycle with nanometer-sized cavities was successfully designed and synthesized, showing excellent adsorption capacity for benzene. The compound can effectively separate benzene from a mixture of benzene and cyclo-hexane, with high purity and easy recycling.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Diverse reactivity of alkynes in C-H activation reactions

Shyam Kumar Banjare et al.

Summary: Alkynes play a crucial role as coupling partners in transition metal-catalysed reactions. Their ability to effectively coordinate with metal d-orbitals makes them highly versatile for the synthesis of valuable organic molecules. Despite extensive research, there is still a lot more to explore in terms of the reactivity of alkynes and their potential applications.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Multiple annulations of inert C(sp2)-H bonds with alkynes

Arijit Saha et al.

Summary: Transition-metal catalyzed directing group assisted annulation of inert C-H bonds is a method for constructing complex molecular frameworks from readily accessible substrates. It allows the activation of directed inert C-H bonds and migration of transition metals, leading to the formation of structurally diverse fused pi-extended (hetero)cycles. The coordination preference of the directing group heteroatom determines the chemo- and regio-selectivity of the transformation. This study emphasizes the conceptual development of unsymmetrical multiple annulation of arene C(sp(2))-H bonds with alkynes, which is highly important.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Applied

Synthesis of Fluorescent 4-Azapyrenes by Palladium(II)-Catalyzed Dual C-H Bond Activation and Annulation

Huan-Chang Hsiao et al.

Summary: Novel dual-emissive and deep-blue/green fluorescent multi-substituted 4-azapyrenes with bathochromic shift emission, high quantum yields up to 0.60, and long excited-state lifetime were successfully synthesized by annulative pi-extension reactions, involving palladium-catalyzed dehydrogenative annulation and superacid-mediated cyclization.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed C-H Bond Functionalization of 2-Pyridones with Alkynes: Switchable Alkenylation, Alkenylation/Directing Group Migration and Rollover Annulation

Xin Xu et al.

Summary: A Cp*Rh(III)-catalyzed chelation-assisted direct C-H bond functionalization has been achieved, giving three different products from internal alkynes in controllable manner. These reaction manifolds offer a divergent access to valuable products with excellent regio- and stereoselectivity.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Ni-Catalyzed Dual C-H Annulation of Benzimidazoles with Alkynes for Synthesis of π-Extended Heteroarenes

Shao-Long Qi et al.

Summary: The study successfully demonstrated the dual C-H annulation of N-aromatic imidazole using a base-metal Ni catalyst, yielding a range of desired polycyclic aza-quinolines in 48-95% yields. The use of bifunctional phosphine oxide ligand was crucial for the success of the reaction.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Harnessing Rhodium-Catalyzed C-H Activation: Regioselective Cascade Annulation for Fused Polyheterocycles

Maneesh Kumar Reddy Singam et al.

Summary: In this study, a new rhodium(III) catalyzed assembly of polyheterocyclic scaffolds has been demonstrated by activating C-H bonds and regioselective annulation of 4-arylbut-3-yn-1-amines with 4-hydroxy-2-alkynoates. Heterocyclization and transmetalation prior to annulation play a key role in initiating this relay redox-neutral catalytic cascade.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Rh(III)-Catalyzed Regioselective Annulations of 3-Arylisoxazolones and 3-Aryl-1,4,2-dioxazol-5-ones with Propargyl Alcohols: Access to 4-Arylisoquinolines and 4-Arylisoquinolones

Tong-Tong Wang et al.

Summary: A novel reaction method has been developed for the synthesis of 4-arylisoquinolones using 3-arylisoxazolones and propargyl alcohols. This research expands the potential applications of isoxazolones in organic synthesis and important biological compound synthesis.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy

Bo-Sheng Zhang et al.

Summary: In the Catallani-Lautens reaction system, a highly selective C-N coupling reaction was achieved by recovering the ortho effect, leading to a one-step synthesis of highly functionalized tricyclic indole derivatives.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Rh(iii)-Catalyzed and synergistic dual directing group-enabled redox-neutral [3+3] annulation of N-phenoxyacetamides with α-allenols

Fangyuan Chen et al.

Summary: This study successfully utilized alpha-allenols as innovative three-carbon annulation components in the Rh(iii)-catalyzed redox-neutral C-H coupling of N-phenoxyacetamides, leading to the assembly of 4-alkylidene chroman-2-ol frameworks through an unusual [3+3] annulation. Mechanistic studies revealed that synergistic coordination modes between the dual directing groups and the rhodium metal center are responsible for the observed exclusive selectivity in this transformation.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

Synthesis of tetracyclic indenopyrazolopyrazolones through cascade reactions of aryl azomethine imines with propargyl alcohols

Linghua Zhang et al.

Summary: This paper presents a novel and efficient synthesis method for tetracyclic indenopyrazolopyrazolone derivatives through cascade reactions, demonstrating advantages of accessibility and potential pharmaceutical applications.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Applied

Propargylic Alcohols as Coupling Partners in Transition-Metal-Catalyzed Arene C-H Activation

Gadi Ranjith Kumar et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Physical

Phenol-Directed C-H Functionalization

Zheng Huang et al.

ACS CATALYSIS (2019)

Article Chemistry, Organic

Rhodium(iii)-catalyzed tandem annulation reaction to build polycyclic benzothiazine derivatives

Yang Li et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Article Chemistry, Multidisciplinary

One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration

Johnathon D. Dooley et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Applied

Rhodium-Catalyzed Synthesis of Multiaryl-substituted Naphthols via a Removable Directing Group

Lianhui Wang et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp2)-H Functionalization/Annulation Reaction

Jun Zheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C-H Functionalizations

David J. Burns et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Rhodium-catalyzed direct coupling of biaryl pyridine derivatives with internal alkynes

Jun Zheng et al.

CHEMICAL COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

Direct Access to Benzo[b]furans through Palladium-Catalyzed Oxidative Annulation of Phenols and Unactivated Internal Alkynes

Malleswara Rao Kuram et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)-H Bond Activation Approach

Jiang Nan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Chemistry, Multidisciplinary

Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion

BM Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)