Enantioselective C-H functionalization reactions enabled by cobalt catalysis

Review Chemistry, Multidisciplinary

Recent Advances in the High-Valent Cobalt-Catalyzed C-H Functionalization of N-Heterocycles

Devesh Chandra et al.

Summary: This review briefly introduces the recent progress in the high-valent cobalt complexes catalyzed C-H functionalization of N-containing heterocycles.

CHEMICAL RECORD (2022)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantioselective C-H Arylation of Indoles

Nicolas Jacob et al.

Summary: In this study, an unprecedented 3d-metal-catalyzed atroposelective direct arylation was reported, leading to the synthesis of rare C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism with oxidative addition as the rate- and enantio-determining step. The use of an unusual N-heterocyclic carbene ligand bearing a remote substituent, along with attractive dispersion interactions and C-H···π interactions, contributed to the excellent enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Cobalt/Salox-Catalyzed Enantioselective C-H Functionalization of Arylphosphinamides

Qi-Jun Yao et al.

Summary: This study reports an unprecedented enantioselective C-H functionalization enabled by a simple cobalt/salicyloxazoline (Salox) catalysis. Chiral Salox ligands can be easily prepared in one step and used for the synthesis of various P-stereogenic compounds with high yields and excellent enantioselectivities. The isolation and characterization of several intermediates provide insights into the mechanism of active catalytic cobalt species generation, the action of Salox ligands, and the mode of stereocontrol.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Cobalt(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective Synthesis of Benzothiadiazine-1-oxides via C-H Activation

Yuki Hirata et al.

Summary: In this study, the combination of an achiral cobalt(III) catalyst and a pseudo-C-2-symmetric H-8-binaphthyl chiral carboxylic acid was utilized for the asymmetric synthesis of benzothiadiazine-1-oxides containing a chiral sulfur center. The optimized protocol achieved high enantioselectivity and allowed for the synthesis of benzothiadiazine-1-oxides with various functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Enantioselective Cobalt-Catalyzed C-H Functionalization

Weiwei Xu et al.

Summary: Enantioselective control in co-catalyzed C-H functionalization has been a challenging task. However, recent progress in this field has led to the development of efficient strategies. This review provides a detailed summary of the critical progress, current challenges, and future trends.

SYNTHESIS-STUTTGART (2022)

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Article Chemistry, Physical

Synthesis of Sulfur-Stereogenic Sulfoximines via Co(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective C-H Amidation

Yi-Bo Zhou et al.

Summary: In this study, we report the synthesis of sulfur-stereogenic sulfoximines through Co(III)/chiral carboxylic acid-catalyzed reaction. The synthetic yields and enantioselectivities are high, and the products can be further transformed into recyclable chiral auxiliaries.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C-H alkenylations

Cong Shen et al.

Summary: An efficient method for the preparation of aryl 1,3-dienes from styrenes and olefins has been developed, utilizing a transient chiral auxiliary derived from aldehydes. The generality of this protocol was demonstrated by the smooth conversion of various 2-vinyl benzaldehyde derivatives, resulting in high yields and excellent enantioselectivities. The derived axially chiral carboxylic acid was found to be a more efficient ligand in the Cp*Co(iii)-catalyzed asymmetric C(sp(3))-H alkylation.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Multidisciplinary

Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization

Kristers Ozols et al.

Summary: The study presents a method for highly enantioselective intermolecular carboaminations of alkenes through C-H activation catalyzed by high-valent cyclopentadienyl cobalt complexes. This method converts widely available acrylates and bicyclic olefins into enantioenriched isotyrosine derivatives and amino-substituted bicyclic scaffolds under very mild conditions. The reactivity outlined in this research is unique to the (CpCoIII)-Co-x complexes and complements the reactivity of 4d- and 5d- precious-metal catalysts.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Physical

Insights into the Mechanism of Low-Valent Cobalt-Catalyzed C-H Activation

Joao C. A. Oliveira et al.

Summary: The use of cobalt complexes of N-heterocycle carbene (NHC) ligands as catalysts for C-H activation is advantageous due to low costs and high efficiencies at room temperature. Detailed computational studies support a mechanism via low-valent cobalt-catalyzed C-H activations, indicating a key C-H metalation via a ligand-to-ligand hydrogen transfer (LLHT) pathway instead of a classical oxidative addition mechanism.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation

Yan-Hua Liu et al.

Summary: The study reports a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by tailor-made amino acid ligands. A novel noncovalent interaction was found critical for the chiral induction, resulting in high yields and excellent enantioselectivities of C2-alkylated indoles. DFT calculations revealed the reaction mechanism and origins of chiral induction in the stereodetermining alkene insertion step.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Physical

Metallaphotoredox Dearomatization of Indoles by a Benzamide-Empowered [4+2] Annulation: Facile Access to Indolo[2,3-c]isoquinolin-5-ones

Yong-Liang Ban et al.

Summary: A metallaphotoredox catalysis protocol has been developed for the efficient dearomatization of indoles using readily available N-quinolyl benzamides under environmentally benign conditions. The reaction allows regioselective functionalization of indoles and provides a mild and economical approach to produce a diverse array of products. Preliminary mechanistic studies suggest a single-electron transfer process is involved, with a catalytically competent organometallic Co(bzac)(3) identified.

ACS CATALYSIS (2021)

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Article Chemistry, Physical

Chiral Carboxylic Acid Assisted Enantioselective C-H Activation with Achiral CpxMIII (M = Co, Rh, Ir) Catalysts

Tatsuhiko Yoshino et al.

Summary: Enantioselective C-H functionalization is a powerful tool for synthesizing chiral molecules. The combination of high-valent group 9 metals with achiral Cp-x ligands and chiral carboxylic acids has shown promise in enabling selective cleavage and functionalization of enantiotopic C-H bonds. This Perspective provides a detailed summary of the background, catalyst design, applied reactions, and future directions in this field.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Synthesis of Chiral Spirolactams via Sequential C-H Olefination/Asymmetric [4+1] Spirocyclization under a Simple CoII/Chiral Spiro Phosphoric Acid Binary System

Wen-Kui Yuan et al.

Summary: An unprecedented enantioselective synthesis of spiro-gamma-lactams was achieved using a simple Co-II/chiral spiro phosphoric acid binary system, resulting in high levels of enantioselectivity. Additionally, a concise synthesis of an aldose reductase inhibitor was successfully carried out under this system.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Synthesis of Atropisomers by Transition-Metal-Catalyzed Asymmetric C-H Functionalization Reactions

Chen-Xu Liu et al.

Summary: Transition-metal-catalyzed enantioselective C-H functionalization is an efficient atom-economic strategy for the synthesis of atropisomers, with a focus on asymmetric catalysis via Pd, Rh, and Ir complexes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Physical

Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component C-H Functionalization

Ana G. Herraiz et al.

Summary: Catalytic enantioselective C-H functionalization has become a tool for creating stereogenic centers, but remains a challenge. A three-component C-H functionalization catalyzed by an earth-abundant Co(III) complex with high enantioselectivity has been described, providing a rapid access to substituted beta-hydroxyketones. The outlined reactivity of (CpCo)-Co-x(III) catalysis shows a higher and exploitable propensity for selective additions across carbonyls compared to Rh(III) chemistry.

ACS CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

C-H bond functionalization by high-valent cobalt catalysis: current progress, challenges and future perspectives

Lukass Lukasevics et al.

Summary: High-valent cobalt catalysis has become a valuable tool for C-H activation and functionalization, attracting more attention as an alternative to noble metal catalysts. The use of Cp*Co(iii) complexes and Co(ii), Co(iii) salts in combination with bidentate chelation assistance has been widely employed in the development of new transformations.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Cobalt-catalyzed diastereo- and enantioselective allyl addition to aldehydes and α-ketoesters through allylic C-H functionalization

Haiyan Zhang et al.

Summary: The development of catalytic generation of allyl-metal complexes through allylic C-H cleavage of alkenes provides a straightforward approach for introducing a versatile allyl group into organic molecules. A multi-tasking chiral catalyst has been identified, which controls the formation of the allyl-cobalt complex and addition to carbonyls with high yield and stereoselectivity, potentially leading to enantioselective transformations of nucleophilic organometallic complexes.

CELL REPORTS PHYSICAL SCIENCE (2021)

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Article Chemistry, Organic

Cp*CoIII/Chiral Carboxylic Acid-Catalyzed Enantioselective 1,4-Addition Reactions of Indoles to Maleimides

Takumaru Kurihara et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Diverse Approaches for Enantioselective C-H Functionalization Reactions Using Group 9 CpxMIII Catalysts

Tatsuhiko Yoshino et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Review Chemistry, Multidisciplinary

Cobalt-Catalyzed Oxidative C-H Activation: Strategies and Concepts

Ruhuai Mei et al.

CHEMSUSCHEM (2020)

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Article Chemistry, Multidisciplinary

Divergent Synthesis of Tunable Cyclopentadienyl Ligands and Their Application in Rh-Catalyzed Enantioselective Synthesis of Isoindolinone

Wen-Jun Cui et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

Andrew Whyte et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Intermolecular Hydroacylation of 1,6-Enynes

Andrew Whyte et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Physical

Site-selective alkene borylation enabled by synergistic hydrometallation and borometallation

Xiaolong Yu et al.

NATURE CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Atroposelective Oxidative C-H/C-H Cross-Coupling Reaction of 1-Aryl Isoquinoline Derivatives with Electron-Rich Heteroarenes

Qiang Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Physical

Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization

Tapas Kumar Achar et al.

ACS CATALYSIS (2020)

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Review Chemistry, Multidisciplinary

Recent advances in oxidative allylic C-H functionalization via group IX-metal catalysis

Amaan M. Kazerouni et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Multidisciplinary

Asymmetric C-H Bond Functionalization of Ferrocenes: New Opportunities and Challenges

Chen-Xu Liu et al.

TRENDS IN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C-H Functionalizations

Kristers Ozols et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Organic

Cp*Co(III)/MPAA-Catalyzed Enantioselective Amidation of Ferrocenes Directed by Thioamides under Mild Conditions

Yan-Hua Liu et al.

ORGANIC LETTERS (2019)

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Review Chemistry, Multidisciplinary

Enantioselective C-H Activation with Earth-Abundant 3d Transition Metals

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Inorganic & Nuclear

Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp3)-H Activation of Thioamides

Daichi Sekine et al.

ORGANOMETALLICS (2019)

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Review Chemistry, Physical

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Johannes Diesel et al.

ACS CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (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 Chemistry, Multidisciplinary

Enantioselective C-H Bond Functionalizations by 3d Transition-Metal Catalysts

Lukasz Wozniak et al.

TRENDS IN CHEMISTRY (2019)

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Review Chemistry, Organic

Recent advances in cobalt-catalysed C-H functionalizations

Alessio Baccalini et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Article Chemistry, Multidisciplinary

Enantioselective Cobalt(III)-Catalyzed C-H Activation Enabled by Chiral Carboxylic Acid Cooperation

Fabio Pesciaioli et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

Cobalt Catalysis for Enantioselective Cyclobutanone Construction

Daniel K. Kim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Organic

Co-Catalyzed Direct Addition of Allylic C(sp3)-H Bonds to Ketones

Tsuyoshi Mita et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Microwave-Assisted Cp*CoIII-Catalyzed C-H Activation/Double C-N Bond Formation Reactions to Thiadiazine 1-Oxides

Jiapian Huang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)-H Bonds

Peng Wen Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Asymmetric Iron-Catalyzed C-H Alkylation Enabled by Remote Ligand meta-Substitution

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Capturing Elusive Cobaltacycle Intermediates: A Real-Time Snapshot of the Cp*CoIII-Catalyzed Oxidative Alkyne Annulation

Jesus Sanjose-Orduna et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Review Chemistry, Multidisciplinary

Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes

Christopher G. Newton et al.

CHEMICAL REVIEWS (2017)

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Review Chemistry, Applied

(Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed C-H Bond Functionalization: From Discovery to Unique Reactivity and Selectivity

Tatsuhiko Yoshino et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantio- and Diastereoselective Intramolecular Hydroacylation of Trisubstituted Alkenes

Junfeng Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

General Enantioselective C-H Activation with Efficiently Tunable Cyclopentadienyl Ligands

Zhi-Jun Jia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Review Chemistry, Physical

Cobalt-Catalyzed C-H Activation

Marc Moselage et al.

ACS CATALYSIS (2016)

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Article Chemistry, Multidisciplinary

Unnatural Amino Acid Synthesis Enabled by the Regioselective Cobalt(III)-Catalyzed Intermolecular Carboamination of Alkenes

Andreas Lerchen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade

Jeffrey A. Boerth et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Review Chemistry, Physical

High-Valent-Cobalt-Catalyzed C-H Functionalization Based on Concerted Metalation-Deprotonation and Single-Electron-Transfer Mechanisms

Donghui Wei et al.

CHEMCATCHEM (2016)

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Article Chemistry, Multidisciplinary

Comparative Catalytic Activity of Group 9 [Cp*MIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents

Juhyeon Park et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts

Rajagopal Santhoshkumar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes

Pin-Sheng Lee et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed, Aminoquinoline-Directed C(sp2)-H Bond Alkenylation by Alkynes

Liene Grigorjeva et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Review Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Transformations

Helene Pellissier et al.

CHEMICAL REVIEWS (2014)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins

Junfeng Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Asymmetric [2+2+2] Cyclization of 1,6-Enynes and Aldehydes

Mana Ishida et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

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Review Multidisciplinary Sciences

Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

Huw M. L. Davies et al.

NATURE (2008)

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Enantioselective C-H functionalization reactions enabled by cobalt catalysis

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