Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C-H Alkenylation/Directing Group Migration

Review Chemistry, Applied

Recent Advances in the Synthesis of C2-Functionalized Pyridines and Quinolines Using N-Oxide Chemistry

Dong Wang et al.

Summary: Recent progress has been made in the direct C-H functionalization of azines, but limitations still exist. In contrast, C2-functionalized pyridines and quinolines can be easily synthesized under appropriate activation conditions.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Additive-Controlled Divergent Synthesis of Tetrasubstituted 1,3-Enynes and Alkynylated 3H-Pyrrolo[1,2-a]indol-3-ones via Rhodium Catalysis

Fei Zhao et al.

Summary: This method reports the controlled divergent synthesis of tetrasubstituted 1,3-enynes and alkynylated 3H-pyrrolo[1,2-a]indol-3-ones through rhodium-catalyzed reactions, featuring excellent selectivity, broad substrate scope, moderate to high yields, and good functional group compatibility under mild redox-neutral conditions.

ORGANIC LETTERS (2021)

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Article Chemistry, Physical

Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study

Fei Zhao et al.

Summary: The Rh(III)-catalyzed domino C-H coupling of N-carbamoyl indoles and 4-hydroxy-2-alkynoates enables the streamlined assembly of highly functionalized furan-2(5H)-ones. This method is characterized by efficient multistep cascade triggered by C-H activation, excellent selectivity, and potential biological applications.

ACS CATALYSIS (2021)

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Article Chemistry, Organic

Temperature-Controlled Divergent Synthesis of Tetrasubstituted Alkenes and Pyrrolo[1,2-a]indole Derivatives via Iridium Catalysis

Siyu Liu et al.

Summary: This novel method demonstrates excellent regio- and stereoselectivity, good substrate scope, and mild redox-neutral conditions, making it a versatile and efficient strategy for synthesizing tetrasubstituted alkenes and pyrrolo[1,2-a]indole derivatives.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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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)

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Article Chemistry, Organic

Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation

Sanjeev Kumar et al.

Summary: The Rh(III)-catalyzed [3+2] annulations and C2-alkenylations of indoles with 1,3-diynes described in this study deliver synthetically important 3H-pyrrolo[1,2-a]indol-3-ones and highly functionalized tetrasubstituted olefin derivatives, with high efficiency and broad functional group compatibility. Additionally, the method has been successfully extended to the synthesis of bis-annulated and trisubstituted alkenes, as well as for the core structure synthesis of protein kinase C inhibitors and melatonin analogues.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Applied

Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes

Fei Zhao et al.

Summary: This study achieved the synthesis of functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones by utilizing electron-deficient alkynes as unconventional C-1 synthons in a redox-neutral rhodium(III)-catalyzed [4+1] annulation. The process exhibited high chemo- and regioselectivity, broad substrate scope, good tolerance of functional groups, moderate to high yields, and mild redox-neutral conditions, providing a robust method to access valuable 1H-imidazo[1,5-a]indol-3(2H)-ones.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Redox-Neutral Rhodium(III)-Catalyzed Chemospecific and Regiospecific [4+1] Annulation between Indoles and Alkenes for the Synthesis of Functionalized Imidazo[1,5-a]indoles

Fei Zhao et al.

Summary: This method utilizes internal alkenes embedded with an oxidizing function/leaving group as a rare onecarbon unit for a redox-neutral rhodium(III)-catalyzed chemo- and regiospecific [4+1] annulation, leading to the synthesis of functionalized imidazo[1,5-a]indoles with excellent chemo- and regioselectivity.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Rh(III)-Catalyzed Divergent Synthesis of Alkynylated Imidazo[1,5-a]indoles and α,α-Difluoromethylene Tetrasubstituted Alkenes

Fei Zhao et al.

Summary: In this study, alkynylated imidazo[1,5-a]indoles and alpha,alpha-difluoromethylene tetrasubstituted alkenes were successfully synthesized via Rh(III)-catalyzed [4 + 1] annulation/alkyne moiety migration and C-H alkenylation/DG migration, showing excellent product selectivity, high yields, and good tolerance of functional groups.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Cobalt(III)-Catalyzed Regioselective C6 Olefination of 2-Pyridones Using Alkynes: Olefination/Directing Group Migration and Olefination

Xin Xu et al.

Summary: A highly regio- and stereoselective direct C6 olefination of 2-pyridones with alkynes using Co(III) catalysis and chelation assistance has been developed. Varying reaction conditions allows for different pathways to achieve tetrasubstituted 6-vinyl-2-pyridones or C6-olefinated 2-pyridones. The protocol features 100% atom economy, excellent site selectivity, high stereoselectivity, and good compatibility of functional groups, with experimental and theoretical studies providing mechanistic insight.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Redox-neutral rhodium(iii)-catalyzed chemo- and regiospecific [4+1] annulation between benzamides and alkenes for the synthesis of functionalized isoindolinones

Jin Qiao et al.

Summary: In this study, an electron-deficient alkene embedded with an oxidizing function/leaving group was used as a rare and nontraditional C-1 synthon to achieve a redox-neutral Rh(iii)-catalyzed chemo- and regioselective [4 + 1] annulation of benzamides for the synthesis of functionalized isoindolinones. This method demonstrated a broad substrate scope, good to excellent yields, excellent chemo- and regioselectivity, good tolerance of functional groups, and mild external-oxidant-free conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Directing group migration strategy in transition-metal-catalysed direct C-H functionalization

Yingtao Wu et al.

Summary: Directing group migration has emerged as a practical strategy for transition-metal-catalysed direct C-H activation, leading to highly atom-economical processes and enabling the reusage of directing groups. Progress has been made in developing multitasking directing groups, with the focus on different types of migratable directing groups and their mechanisms, as well as synthetic applications.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Recent advances in the stereoselective synthesis of acyclic all-carbon tetrasubstituted alkenes

Floris Buttard et al.

Summary: This review article presents the most significant developments in the field of tetrasubstituted alkenes from 2007 to 2020, focusing on mechanisms and remaining limitations of contemporary methods, including internal alkyne carbofunctionalizations, multicomponent couplings, and other cross-coupling reactions.

CHEMICAL COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

N-Heterocyclic Carbene Complexes in C-H Activation Reactions

Qun Zhao et al.

CHEMICAL REVIEWS (2020)

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Article Chemistry, Applied

Rhodium-Catalyzed Cascade Reactions of Indoles with 4-Hydroxy-2-Alkynoates for the Synthesis of Indole-Fused Polyheterocycles

Xiaowei Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Physical

Domino C-H Activation/Directing Group Migration/Alkyne Annulation: Unique Selectivity by d6-Cobalt(III) Catalysts

Cuiju Zhu et al.

ACS CATALYSIS (2020)

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Article Chemistry, Physical

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

Fei Zhao et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Rhodium(III)-Catalyzed C-H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes

Xiaowei Wu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

The ruthenium(ii)-catalyzed C-H olefination of indoles with alkynes: the facile construction of tetrasubstituted alkenes under aqueous conditions

Ming Li et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Review Chemistry, Organic

Chelation-assisted transition metal-catalysed C-H chalcogenylations

Wenbo Ma et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Review Chemistry, Applied

Recent Advances in Ruthenium(II)-Catalyzed C-H Bond Activation and Alkyne Annulation Reactions

G. Duarah et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Biochemistry & Molecular Biology

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

Xiuwen Jia et al.

MOLECULES (2019)

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Article Pharmacology & Pharmacy

Pharmacokinetic study of imrecoxib in patients with renal insufficiency

Qi Pei et al.

EUROPEAN JOURNAL OF CLINICAL PHARMACOLOGY (2019)

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Article Chemistry, Applied

Gold-catalyzed Rapid Construction of Nitrogen-containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Jin Qiao et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Review Chemistry, Physical

Manganese-Catalyzed C-H Olefination Reactions

Yuanyuan Hu et al.

CHEMCATCHEM (2019)

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Review Chemistry, Multidisciplinary

3d Transition Metals for C-H Activation

Parthasarathy Gandeepan et al.

CHEMICAL REVIEWS (2019)

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Review Biochemistry & Molecular Biology

Recent Advances in the Addition of Amide/Sulfonamide Bonds to Alkynes

Fei Zhao et al.

MOLECULES (2019)

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Review Chemistry, Multidisciplinary

Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation

Zhen Chen et al.

CHEMICAL SOCIETY REVIEWS (2019)

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Review Chemistry, Multidisciplinary

Increasing Catalyst Efficiency in C-H Activation Catalysis

Tobias Gensch et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Review Chemistry, Multidisciplinary

Ruthenium-Mediated Distal C-H Activation

Farheen Fatima Khan et al.

CHEMISTRY-AN ASIAN JOURNAL (2018)

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Review Chemistry, Multidisciplinary

Mechanistic view of Ru-catalyzed C-H bond activation and functionalization: computational advances

Chunhui Shan et al.

CHEMICAL SOCIETY REVIEWS (2018)

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Article Chemistry, Organic

Rhodium(III)-Catalyzed Redox-Neutral Cascade [3+2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization

Jin-Long Pan et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Organic

Cp*CoIII-Catalyzed CH Alkenylation/Annulation Reactions of Indoles with Alkynes: A DFT Study

Ken Sakata et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Review Chemistry, Organic

Catalytic and catalyst-free diboration of alkynes

Fei Zhao et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Review Chemistry, Organic

Recent advances in positional-selective alkenylations: removable guidance for twofold C-H activation

Wenbo Ma et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Review Chemistry, Multidisciplinary

Regioselective Direct C-Alkenylation of Indoles

Marino Petrini

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Review Chemistry, Multidisciplinary

Computational Studies of Carboxylate-Assisted C-H Activation and Functionalization at Group 8-10 Transition Metal Centers

David L. Davies et al.

CHEMICAL REVIEWS (2017)

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Review Chemistry, Multidisciplinary

Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes

Yudong Yang et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*CoIII-Catalyzed C-H Alkenylation/Directing Group Migration Sequence

Hideya Ikemoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Review Chemistry, Organic

Research Progress in Metal-Catalyzed Addition of Carbon-Hetero Bonds to Alkynes

Fei Zhao et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2017)

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Review Chemistry, Multidisciplinary

A Simple and Versatile Amide Directing Group for C-H Functionalizations

Ru-Yi Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

The ruthenium-catalysed selective synthesis of mono-deuterated terminal alkynes

Basujit Chatterjee et al.

CHEMICAL COMMUNICATIONS (2016)

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Review Chemistry, Multidisciplinary

Alkenylation of Arenes and Heteroarenes with Alkynes

Vadim P. Boyarskiy et al.

CHEMICAL REVIEWS (2016)

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Review Chemistry, Multidisciplinary

Mild metal-catalyzed C-H activation: examples and concepts

T. Gensch et al.

CHEMICAL SOCIETY REVIEWS (2016)

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Article Chemistry, Medicinal

Design, Synthesis, and Biological Evaluation of Indoline and Indole Derivatives as Potent and Selective α1A-Adrenoceptor Antagonists

Fei Zhao et al.

JOURNAL OF MEDICINAL CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

Highly selective intramolecular addition of C-N and S-N bonds to alkynes catalyzed by palladium: a practical access to two distinct functional indoles

Chenglin Wu et al.

RSC ADVANCES (2016)

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Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-N Bond Forming Reactions Using Organic Azides as the Nitrogen Source: A Journey for the Mild and Versatile C-H Amination

Kwangmin Shin et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Review Chemistry, Organic

Recent advances in the ruthenium-catalyzed hydroarylation of alkynes with aromatics: synthesis of trisubstituted alkenes

Rajendran Manikandan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed intramolecular addition of C-N bond to alkynes: a novel approach to 3-diketoindoles

Chenglin Wu et al.

RSC ADVANCES (2015)

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Review Chemistry, Multidisciplinary

Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles

Xun-Xiang Guo et al.

CHEMICAL REVIEWS (2015)

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Review Chemistry, Applied

Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation

Suman De Sarkar et al.

ADVANCED SYNTHESIS & CATALYSIS (2014)

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Review Chemistry, Multidisciplinary

Functional group directed C-H borylation

A. Ros et al.

CHEMICAL SOCIETY REVIEWS (2014)

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Article Chemistry, Inorganic & Nuclear

A mixed-valence dinuclear ruthenium complex composed of Ru(II)-acetylide and Ru(III)-tropolonato units: Acetylide-vinylidene interconversion in solution and solid state

Jun Yoshida et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2014)

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Article Chemistry, Inorganic & Nuclear

Ancillary Metal Centers in Frustrated Lewis Pair Chemistry: Ruthenium Acetylide as a Lewis Base in the Activation of CO2, Aldehyde, and Alkyne

Michael P. Boone et al.

ORGANOMETALLICS (2014)

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Article Multidisciplinary Sciences

A multitasking functional group leads to structural diversity using designer C-H activation reaction cascades

Ying Chen et al.

NATURE COMMUNICATIONS (2014)

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Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Redox-Neutral Coupling of N-Phenoxyacetamides and Alkynes with Tunable Selectivity

Guixia Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Review Chemistry, Multidisciplinary

Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions

Denise A. Colby et al.

ACCOUNTS OF CHEMICAL RESEARCH (2012)

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Review Chemistry, Multidisciplinary

Ruthenium(II)-Catalyzed C-H Bond Activation and Functionalization

Percia Beatrice Arockiam et al.

CHEMICAL REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Recent advances in transition metal-catalyzed sp3 C-H amination adjacent to double bonds and carbonyl groups

Thomas A. Ramirez et al.

CHEMICAL SOCIETY REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope

Lutz Ackermann

CHEMICAL REVIEWS (2011)

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Review Chemistry, Multidisciplinary

Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation

Seung Hwan Cho et al.

CHEMICAL SOCIETY REVIEWS (2011)

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Article Chemistry, Multidisciplinary

Searching for green solvents

Philip G. Jessop

GREEN CHEMISTRY (2011)

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Review Chemistry, Multidisciplinary

Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation

Denise A. Colby et al.

CHEMICAL REVIEWS (2010)

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Article Chemistry, Organic

Hydroarylation of Alkynes via Aryl C-H Bond Cleavage

Xulun Wang et al.

CURRENT ORGANIC CHEMISTRY (2010)

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Article Chemistry, Medicinal

Preparation and Evaluation of Carborane Analogues of Tamoxifen

Michael L. Beer et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

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Article Medicine, General & Internal

Amlodipine: a pharmacoeconomic review

Simona de Portu et al.

JOURNAL OF MEDICAL ECONOMICS (2010)

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Review Chemistry, Organic

Transition-Metal-Catalyzed Hydroarylation Reactions of Alkynes Through Direct Functionalization of C-H Bonds: A Convenient Tool for Organic Synthesis

Tsugio Kitamura

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2009)

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Article Chemistry, Multidisciplinary

Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant

Dong-Hui Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Review Chemistry, Multidisciplinary

Stereocontrolled synthesis of tetrasubstituted olefins

Alison B. Flynn et al.

CHEMICAL REVIEWS (2007)

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Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C-H Alkenylation/Directing Group Migration

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