Mechanistic Insight into Rh-Catalyzed C(sp2)–O Bond Cleavage Applied to Cross-Coupling Reaction of Benzofurans with Aryl Grignard Reagents
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Title
Mechanistic Insight into Rh-Catalyzed C(sp2)–O Bond Cleavage Applied to Cross-Coupling Reaction of Benzofurans with Aryl Grignard Reagents
Authors
Keywords
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Journal
ACS Catalysis
Volume 12, Issue 13, Pages 7936-7949
Publisher
American Chemical Society (ACS)
Online
2022-06-20
DOI
10.1021/acscatal.2c01974
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Note: Only part of the references are listed.- Selective C–O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium–Aluminum Heterobimetallic Complex
- (2021) Rin Seki et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- The Anionic Pathway in Nickel‐Catalysed Cross‐Coupling of Aryl Ethers
- (2021) Andryj Borys et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Nickel‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Involving C−O Bond Activation
- (2021) Aoi Morishige et al. HELVETICA CHIMICA ACTA
- Recent Advances in Continuous‐Flow Enantioselective Catalysis
- (2020) Tao Yu et al. CHEMISTRY-A EUROPEAN JOURNAL
- Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)–O Bonds Enabled by Chromium Catalysis
- (2020) Jinghua Tang et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage
- (2020) Zihang Qiu et al. CHEMICAL REVIEWS
- Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
- (2020) Lei Tao et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Synthesis of and Structural Insights into Contact Ion Pair and Solvent-Separated Ion Pair Diphenyliridate Complexes
- (2020) Takanori Iwasaki et al. ORGANOMETALLICS
- Chemodivergence Between Electrophiles in Cross‐Coupling Reactions
- (2020) Emily K Reeves et al. CHEMISTRY-A EUROPEAN JOURNAL
- Harnessing C–O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions
- (2020) Elizabeth R. Jarvo et al. SYNLETT
- Nickel Carbodicarbene Catalyzes Kumada Cross-Coupling of Aryl Ethers with Grignard Reagents through C-O Bond Activation
- (2019) Ram Ambre et al. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
- Advances in Transition Metal‐Catalyzed Selective Functionalization of Inert C−O Bonds Assisted by Directing Groups
- (2019) Cong Lin et al. ADVANCED SYNTHESIS & CATALYSIS
- Flow Technology for Genesis and Use of (Highly) Reactive Organometallic Reagents
- (2019) Marco Colella et al. CHEMISTRY-A EUROPEAN JOURNAL
- Modular Arene Difunctionalization of Unactivated C–O and C–H Bonds by Sequential Chromium-Catalyzed Transformations
- (2019) Zhi Rong et al. ORGANIC LETTERS
- Chemodivergent Nickel(0)-Catalyzed Arene C–F Activation with Alkynes: Unprecedented C–F/C–H Double Insertion
- (2019) Lorena Capdevila et al. ACS Catalysis
- Copper-Catalyzed Ring-Opening Silylation of Benzofurans with Disilane
- (2018) Hayate Saito et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Mechanistic Insights into the Ni-Catalyzed Reductive Carboxylation of C−O Bonds in Aromatic Esters with CO2 : Understanding Remarkable Ligand and Traceless-Directing-Group Effects
- (2018) Yan-Li Han et al. Chemistry-An Asian Journal
- Ni-Catalyzed Dimerization and Hydroperfluoroarylation of 1,3-Dienes
- (2018) Takanori Iwasaki et al. JOURNAL OF ORGANIC CHEMISTRY
- Intermediacy of Ni–Ni Species in sp2 C–O Bond Cleavage of Aryl Esters: Relevance in Catalytic C–Si Bond Formation
- (2018) Rosie J. Somerville et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions
- (2018) Takanori Iwasaki et al. Chemical Science
- Cross-coupling polycondensation via C–O or C–N bond cleavage
- (2018) Ze-Kun Yang et al. Nature Communications
- Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers
- (2018) Gavin J. Harkness et al. Catalysis Science & Technology
- Copper-Catalyzed Ring Opening of Benzofurans and Enantioselective Hydroamination Cascade
- (2018) Shuli You et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)–O Bonds with a Traceless Activation Strategy
- (2018) Fei Fan et al. JOURNAL OF ORGANIC CHEMISTRY
- Computational Mechanistic Study on the Nickel-Catalyzed C–H/N–H Oxidative Annulation of Aromatic Amides with Alkynes: The Role of the Nickel (0) Ate Complex
- (2018) Ken Yamazaki et al. ORGANOMETALLICS
- Combined Theoretical and Experimental Studies of Nickel-Catalyzed Cross-Coupling of Methoxyarenes with Arylboronic Esters via C–O Bond Cleavage
- (2017) Martin C. Schwarzer et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C–O Arylation
- (2017) Yuto Kurata et al. ORGANIC LETTERS
- Manganese-Catalyzed Ring Opening of Benzofurans and Its Application to Insertion of Heteroatoms into the C2–O Bond
- (2017) Shun Tsuchiya et al. ORGANIC LETTERS
- Revisitation of Organoaluminum Reagents Affords a Versatile Protocol for C–X (X = N, O, F) Bond-Cleavage Cross-Coupling: A Systematic Study
- (2017) Hiroyuki Ogawa et al. ACS Catalysis
- Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination
- (2016) Xiangqian Liu et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- Nickel-catalyzed Ring-opening Cross-coupling of Cyclic Alkenyl Ethers with Arylboronic Esters via Carbon–Oxygen Bond Cleavage
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- Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides
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- Flow “Fine” Synthesis: High Yielding and Selective Organic Synthesis by Flow Methods
- (2015) Shū Kobayashi Chemistry-An Asian Journal
- Regio- and Chemoselective Kumada–Tamao–Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions
- (2015) Xuefeng Cong et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C–O Bond Cleavage
- (2015) Mamoru Tobisu et al. ORGANIC LETTERS
- Nickel-Catalyzed Alkynylation of Anisoles via C–O Bond Cleavage
- (2015) Mamoru Tobisu et al. ORGANIC LETTERS
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- (2015) Carl J. Mallia et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Mixed NHC/Phosphine Ni(II) Complexes: Synthesis and Their Applications as Versatile Catalysts for Selective Cross-Couplings of ArMgX with Aryl Chlorides, Fluorides, and Methyl Ethers
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- (2014) Matthias Leiendecker et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2014) Xin Hong et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2013) Florence Mongin et al. CHEMICAL REVIEWS
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- (2013) Julio C. Pastre et al. CHEMICAL SOCIETY REVIEWS
- Carbonylation in microflow: close encounters of CO and reactive species
- (2013) Takahide Fukuyama et al. GREEN CHEMISTRY
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- (2011) Honghua Rao et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2008) Bing-Tao Guan et al. CHEMICAL COMMUNICATIONS
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