4.4 Review

Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles

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Article Chemistry, Physical

Ligand-Controlled Selectivity in the Pd-Catalyzed C-H/C-H Cross-Coupling of Indoles with Molecular Oxygen

Igor Beckers et al.

Summary: Two indoles linked by a C-C bond have emerged as promising scaffolds in medicinal chemistry. In this study, selective C-H/C-H cross-coupling of N-substituted indoles without directing groups was achieved under mild conditions, driven by molecular oxygen. The ligand-controlled selectivity can be exploited to achieve selective cross-coupling between two indoles with different substitution patterns.

ACS CATALYSIS (2021)

Article Biochemistry & Molecular Biology

Theoretical studies on the mechanism of Pd2+-catalyzed regioselective C-H alkylation of indole with MesICH2CF3OTf

Yao Shi et al.

Summary: The reaction mechanism of Pd2+-catalyzed regioselective C-H alkylation of indole with MesICH(2)CF(3)OTf has been investigated using density functional theory calculations. The mechanism involves four main steps: C-H activation, oxidative addition, reductive elimination, and ligands substitution. The study finds that the regioselectivity of the reaction can be explained by the different stability of the CMD transition states and the relative stabilities of deprotonated intermediates in the C-H activation step.

JOURNAL OF MOLECULAR MODELING (2021)

Article Chemistry, Multidisciplinary

Ligand-free iridium-catalyzed regioselective C-H borylation of indoles

Zilong Pan et al.

Summary: In this study, a ligand-free Ir-catalyzed C-H borylation of N-acyl protected indoles was reported, providing C3 borylated indoles in good yields with excellent regioselectivities. The method was also demonstrated to be suitable for gram-scale borylation, with the C-B bonds easily converted to C-C and C-heteroatom bonds.

RSC ADVANCES (2021)

Article Chemistry, Inorganic & Nuclear

Theoretical studies on Rh(III)-catalyzed regioselective C-H bond cyanation of indole and indoline

Chao Deng et al.

DALTON TRANSACTIONS (2019)

Article Chemistry, Physical

Mechanism and selectivity of rhodium-catalyzed CH bond arylation of indoles

Stefano Santoro et al.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2018)

Article Multidisciplinary Sciences

Rhodium-catalyzed, P-directed selective C7 arylation of indoles

Xiaodong Qiu et al.

SCIENCE ADVANCES (2018)

Article Chemistry, Multidisciplinary

Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position

Arun Jyoti Borah et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles

Lanting Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Applied

Transition Metal-Catalyzed C-H Activation of Indoles

Alexander H. Sandtorv

ADVANCED SYNTHESIS & CATALYSIS (2015)

Article Chemistry, Applied

Rhodium(III)-Catalyzed Selective C-H Cyanation of Indolines and Indoles with an Easily Accessible Cyano Source

Neeraj Kumar Mishra et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed C-H Cyanation of Arenes and Heteroarenes

Jie Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Applied

Zinc-Catalyzed Direct Cyanation of Indoles and Pyrroles: Nitromethane as a Source of a Cyano Group

Yuta Nagase et al.

ADVANCED SYNTHESIS & CATALYSIS (2014)

Article Chemistry, Multidisciplinary

Iron(II)-Catalyzed Direct Cyanation of Arenes with Aryl(cyano)iodonium Triflates

Zhibin Shu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Pyrroloindolone Synthesis via a Cp*CoIII-Catalyzed Redox-Neutral Directed C-H Alkenylation/Annulation Sequence

Hideya Ikemoto et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Co(III)-Catalyzed C-H Activation/Formal SN-Type Reactions: Selective and Efficient Cyanation, Halogenation, and Allylation

Da-Gang Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Aromatic C-H Bond Cyanation by C-CN Bond Cleavage of Inert Acetonitrile

Xuezhen Kou et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Review Chemistry, Multidisciplinary

N,N-Dimethylformamide: A Multipurpose Building Block

Shengtao Ding et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C-H bonds

Kazuhiro Okamoto et al.

CHEMICAL COMMUNICATIONS (2012)

Article Chemistry, Applied

Iron-Catalyzed C?H Fuctionalization of Indoles

Yan Cai et al.

ADVANCED SYNTHESIS & CATALYSIS (2011)

Review Chemistry, Multidisciplinary

Intermolecular Dehydrogenative Heck Reactions

Jean Le Bras et al.

CHEMICAL REVIEWS (2011)

Review Chemistry, Multidisciplinary

Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

Sandro Cacchi et al.

CHEMICAL REVIEWS (2011)

Article Chemistry, Multidisciplinary

Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization

Shengtao Ding et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions

Thomas W. Lyons et al.

CHEMICAL REVIEWS (2010)

Review Chemistry, Multidisciplinary

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

Anna J. Kochanowska-Karamyan et al.

CHEMICAL REVIEWS (2010)

Article Chemistry, Organic

Palladium-Catalyzed Direct Cyanation of Indoles with K4[Fe(CN)6]

Guobing Yan et al.

ORGANIC LETTERS (2010)

Article Chemistry, Organic

Pd(OAc)2-catalyzed C-H activation of indoles: a facile synthesis of 3-cyanoindoles

B. V. Subba Reddy et al.

TETRAHEDRON LETTERS (2010)

Article Chemistry, Multidisciplinary

Total Synthesis of Celogentin C

Bing Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality

Xiao Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Catalytic Functionalization of Indoles in a New Dimension

Marco Bandini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation

Jared C. Lewis et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Article Chemistry, Multidisciplinary

Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates

Serge I. Gorelsky et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Review Chemistry, Multidisciplinary

Practical methodologies for the synthesis of indoles

Guy R. Humphrey et al.

CHEMICAL REVIEWS (2006)

Article Chemistry, Multidisciplinary

Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ

X Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Review Biochemistry & Molecular Biology

Advances in marine natural products of the indole and annelated indole series: Chemical and biological aspects

U Pindur et al.

CURRENT MEDICINAL CHEMISTRY (2001)