4.7 Article

Rh(III)-Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes

Related references

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

Site-Selective C-H Functionalization of Carbazoles

Mazen Elsaid et al.

Summary: This paper reports the first development of direct Pd-catalyzed C-H alkylation and acylation of carbazoles assisted by norbornene (NBE) as a transient directing mediator. The method does not require the installation of a pre-installed directing group, greatly expanding the applicability of carbazole compounds and improving reaction efficiency.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Multidisciplinary

Iron-catalyzed reductive cyclization of nitroarenes: Synthesis of aza-heterocycles and DFT calculations

Christine Tran et al.

Summary: We developed a new approach for synthesizing substituted dihydrobenzo[c]carbazoles and indoles through iron-catalyzed hydrogen transfer reduction of nitroarenes followed by intramolecular cyclization. This strategy involves the use of a Knolker-type catalyst, Cs2CO3 as the base, and benzyl alcohol as the hydrogen donor. We synthesized 30 examples of aza-heterocycles with moderate to excellent yields using this approach. DFT calculations suggest an anionic mechanism for the reaction pathway.

CHINESE CHEMICAL LETTERS (2023)

Article Chemistry, Organic

Synthesis of 2-(2-Nitroalkyl)indoles by Rhodium(III)-Catalyzed C-H Alkylation

Shuang-Liang Liu et al.

Summary: The Rh(III)-catalyzed addition of indole C2-H bond to nitroalkenes at room temperature and atmospheric pressure is reported, providing a convenient method for the synthesis of a wide range of 2-(2-nitroalkyl)indoles in high yield and selectivity. Pyrrole derivatives were also successfully employed in the Friedel-Crafts alkylation reaction. The obtained nitroalkane products could be further transformed into structurally diverse and valuable indole derivatives. Control experiments were conducted and a plausible mechanism was proposed.

ORGANIC LETTERS (2023)

Review Chemistry, Multidisciplinary

Emergence of Pyrimidine-Based meta-Directing Group: Journey from Weak to Strong Coordination in Diversifying meta-C-H Functionalization

Uttam Dutta et al.

Summary: C-H activation is a powerful synthetic tool to construct complex molecular frameworks. The use of directing groups (DGs) has resolved selectivity issues and offered a unique solution for the synthesis of complex molecules. By using different types of DGs, we achieved distal meta-C-H functionalization and gained a deeper understanding of the mechanism.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

Review Chemistry, Multidisciplinary

Toolbox for Distal C-H Bond Functionalizations in Organic Molecules

Soumya Kumar Sinha et al.

Summary: Transition-metal-catalyzed C-H activation is a contemporary synthetic approach that has significant impact and importance in the synthesis of natural products and pharmaceutical drugs.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

Construction of C2-Quaternary-indol-3-ones via RhIII-Catalyzed [3+2] Spirocyclization from Indole Ketones and Nitroolefins

Wen-Bi Hu et al.

Summary: In this study, novel complex C2-quaternary-indol-3-one units bearing versatile nitro groups were successfully developed from pseudo-indolones and alpha,beta-unsaturated nitroolefins through rhodium-catalyzed C-H activation/[3 + 2] spirocyclization. Notably, four diastereomers could be selectively obtained in the reaction by condition control.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Transition metal-catalyzed regioselective functionalization of carbazoles and indolines with maleimides

Eun Hee Cho et al.

Summary: The selective activation of carbazoles and indolines via transition metal-catalyzed reactions allows for the rapid installation of succinimide groups at specific positions, demonstrating the intrinsic reactivity of indolines and mild reaction conditions to generate succinimide-substituted indoles.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Transition-metal-catalyzed C-H bond alkylation using olefins: recent advances and mechanistic aspects

Debasish Mandal et al.

Summary: Transition metal catalysis has played an important role in C-C bond formation reactions, including alkylation. Compared to traditional methods, transition metal catalysis offers advantages such as fewer reaction steps, shorter reaction times, atom economy, and control over regio- and stereo-selectivity. The hydrocarbonation of alkenes has received increased attention due to its ability to selectively synthesize various industrially and pharmaceutically relevant compounds. This review provides a scientific and systematic analysis of recent developments in transition metal-catalyzed alkylation of C-H bonds using simple and activated olefins, highlighting key features and mechanistic studies.

CHEMICAL SOCIETY REVIEWS (2022)

Review Chemistry, Organic

Recent advances in transition-metal-catalyzed directed C-H alkenylation with maleimides

Shuang-Liang Liu et al.

Summary: Transition-metal-catalyzed directed C-H alkenylation with maleimides has gained significant attention in recent years due to the presence of maleimide core moieties in various natural products and pharmaceuticals. Moreover, these derivatives can be easily transformed into biologically important compounds including succinimides, pyrrolidines, and gamma-lactams. This review provides an overview of the major progress and mechanistic investigations on Heck-type reaction/cyclization of maleimides with organic molecules until early 2022.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Rhodium-catalysed decarbonylative C(sp2)-H alkylation of indolines with alkyl carboxylic acids and carboxylic anhydrides under redox-neutral conditions

Hirotsugu Suzuki et al.

Summary: We developed a new catalytic system for the decarbonylative C(sp(2))-H alkylation of indolines. This method allows for the use of cheap, abundant, and non-toxic alkyl carboxylic acids and their anhydrides as an alkyl source, introducing a primary alkyl chain that was not possible with previous methods.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Mechanochemical Solvent-Free Catalytic C-H Methylation

Shengjun Ni et al.

Summary: This new mechanochemical method enables highly regioselective C-H methylation of (hetero)arenes, showing excellent functional-group compatibility and shorter reaction times, and can be used for the synthesis of biologically active compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via RhIII-Catalyzed Annulation Using Nitroolefins

Pidiyara Karishma et al.

Summary: A mild Rh-catalyzed method was developed for the synthesis of hydroxyimino functionalized indazolo[1,2-a]cinnolines and phthalazino[2,3-a]cinnolines by reductive [4 + 2] annulation between 1-arylindazolones and 2-aryl-2,3-dihydrophthalazine-1,4-diones with varied nitroolefins. The targeted oxime decorated tetracyclic fused cinnolines were synthesized via sequential C-H activation/olefin insertion/reduction under reducing-agent-free conditions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Site-Selective Aerobic C-H Monoacylation of Carbazoles Using Palladium Catalysis

Subhadip Maiti et al.

Summary: This study presents a general palladium-catalyzed monoacylation method for carbazoles, using toluene derivatives as both acyl source and organic solvent, with NHPI and oxygen as cocatalyst and sole oxidant, respectively. The regioselective acylation at C-8 position of monosubstituted N-pyridylcarbazoles is achieved using aldehyde as the acyl source, indicating a highly site-selective acylation proceeding through a radical process.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Organic

Maleimides in Directing-Group-Controlled Transition-Metal-Catalyzed Selective C-H Alkylation

Shuang-Liang Liu et al.

Summary: Maleimides and succinimides are important scaffolds in biological fields, and maleimide derivatives have been extensively used in various organic transformations. Efficient chelation-assisted strategies have been employed for selective addition of C-H bonds to maleimides, producing succinimides which are crucial building blocks in organic synthesis. Significant advances have been made in transition-metal-catalyzed C-H alkylation using maleimides from 2012 to 2021, with discussion on diverse catalysts, substrates, reaction mechanisms, and synthetic applications.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Study on Palladium(II)-Catalyzed Mono-1-alkenylation of 9H-Carbazoles

Dongdong Guo et al.

Summary: The method involves the direct mono-1-alkenylation of 9H-carbazole molecules using divalent palladium as a catalyst and an N-(2-pyridyl)sulfanyl directing group, providing an efficient synthetic route for the synthesis of cross-dialkenylated carbazoles.

SYNLETT (2021)

Review Multidisciplinary Sciences

Arene diversification through distal C(sp2)-H functionalization

Uttam Dutta et al.

Summary: This review summarizes recent elegant discoveries in controlling distal C-H activation through directing group assistance, transient mediators or traceless directors, noncovalent interactions, and catalyst and/or ligand selection.

SCIENCE (2021)

Article Chemistry, Organic

SCpRh(III)-Catalyzed Enantioselective Aryl C-H Addition to Nitroalkenes

Zhi-Jie Wu et al.

Summary: A novel method for the Rh-catalyzed enantioselective direct addition of benzamide C-H bond to nitroalkenes was developed, yielding a range of C-H adducts with good yields and enantioselectivity under mild conditions. The reaction is versatile and can accommodate various functional groups.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Temporary (P=O) directing group enabled carbazole ortho arylation via palladium catalysis

Zhi-Chao Qi et al.

Summary: A palladium-catalyzed, temporary P(O) directing group assisted C-H bond arylation of carbazoles was achieved. The release of the directing group occurs spontaneously in the reaction and mechanistic studies indicate that acid is essential for N-P bond cleavage.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Synthesis and reactivity of carbazole-containing hypervalent iodine(III) reagents

Tianlei Lan et al.

CHINESE CHEMICAL LETTERS (2020)

Review Chemistry, Organic

Application of Readily Available Metals for C-H Activation

Mohammad Dodangeh et al.

CURRENT ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Rh(III)-Catalyzed C2-Alkylation of Indoles with Maleimides at Low Catalyst Loadings

Shuang-Liang Liu et al.

CHEMISTRYSELECT (2020)

Article Chemistry, Organic

RuII-Catalysed Regioselective C-N Bond Formation of Indolines and Carbazole with Acyl Azides

Sonbidya Banerjee et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Inert C-H Bond Transformations Enabled by Organometallic Manganese Catalysis

Yuanyuan Hu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Organic

Rh-III-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes

Tyler J. Potter et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Access to C5-Alkylated Indolines/Indoles via Michael-Type Friedel-Crafts Alkylation Using Aryl-Nitroolefins

Berrak Ertugrul et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry

Carlo Sambiagio et al.

CHEMICAL SOCIETY REVIEWS (2018)

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Transformations of Alkyl C-H Bonds

Jian He et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Physical

Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes

Tyler J. Potter et al.

ACS CATALYSIS (2017)

Article Chemistry, Organic

Copper-Promoted Thiolation of C(sp2)-H Bonds Using a 2-Amino Alkylbenzimidazole Directing Group

Shuang-Liang Liu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Rhodium(III)-Catalyzed C-H Activation of Nitrones and Annulative Coupling with Nitroalkenes

Dachang Bai et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

An Approach to 3-(Indo1-2-yl)succinimide Derivatives by Manganese Catalyzed C-H Activation

Shuang-Liang Liu et al.

ORGANIC LETTERS (2017)

Review Chemistry, Multidisciplinary

Transition metal-catalyzed site- and regio-divergent C-H bond functionalization

Lucy Ping et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Applied

Nickel-Catalyzed Sulfonylation of C(sp2)-H Bonds with Sodium Sulfinates

Shuang-Liang Liu et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Organic

Cerium(III)-catalyzed C3-acylation of indoles with nitroolefins

Cheng-Tao Feng et al.

TETRAHEDRON LETTERS (2016)

Article Chemistry, Multidisciplinary

Ru-Catalyzed highly site-selective C-H bond arylation of 9-(pyrimidin-2-yl)-9H-carbazole

K. Harsha Vardhan Reddy et al.

RSC ADVANCES (2016)

Article Chemistry, Organic

The Palladium-Catalyzed Intermolecular C-H Chalcogenation of Arenes

Renhua Qiu et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Copper-mediated thiolation of carbazole derivatives and related N-heterocycle compounds

Longzhi Zhu et al.

RSC ADVANCES (2015)

Article Chemistry, Physical

PCDTBT: en route for low cost plastic solar cells

Serge Beaupre et al.

JOURNAL OF MATERIALS CHEMISTRY A (2013)

Review Chemistry, Multidisciplinary

Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids

Arndt W. Schmidt et al.

CHEMICAL REVIEWS (2012)

Article Chemistry, Multidisciplinary

A Non-Heme Iron(III) Complex with Porphyrin-like Properties That Catalyzes Asymmetric Epoxidation

Takashi Niwa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Carbazole oligomers revisited: new additions at the carbazole 1-and 8-positions

Wen-Liang Gong et al.

RSC ADVANCES (2012)

Review Chemistry, Multidisciplinary

Organic host materials for phosphorescent organic light-emitting diodes

Youtian Tao et al.

CHEMICAL SOCIETY REVIEWS (2011)

Review Chemistry, Multidisciplinary

Carbazole-based polymers for organic photovoltaic devices

Jiaoli Li et al.

CHEMICAL SOCIETY REVIEWS (2010)

Review Chemistry, Multidisciplinary

Poly(2,7-carbazole)s: Structure-property relationships

Nicolas Blouin et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Review Chemistry, Multidisciplinary

Small-molecule H-bond donors in asymmetric catalysis

Abigail G. Doyle et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Applied

Dioxomolybdenum(VI)-catalyzed reductive cyclization of nitro-aromatics.: Synthesis of carbazoles and indoles

Roberto Sanz et al.

ADVANCED SYNTHESIS & CATALYSIS (2007)

Review Chemistry, Multidisciplinary

Isolation and synthesis of biologically active carbazole alkaloids

HJ Knölker et al.

CHEMICAL REVIEWS (2002)