4.8 Article

Formal C-H/C-I Metathesis: Site-Selective C-H Iodination of Anilines Using Aryl Iodides

Related references

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

Arene C-H Iodination Using Aryl Iodides

Shangda Li et al.

Summary: Metathesis reactions are powerful synthetic tools used in various fields. In this study, the first Pd(II)-catalyzed C-H iodination of arenes was reported, using 2-nitrophenyl iodides as iodinating reagents via a formal metathesis reaction. The reaction exhibited unusual C-I bond formation instead of C-C coupling, allowing for selective iodination of challenging substrates.

CCS CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Distal Ruthenaelectro-Catalyzed meta-C-H Bromination with Aqueous HBr

Yulei Wang et al.

Summary: While electrochemical ortho-selective C-H activations are well established, the development of distal C-H activations is still limited. In this study, we report the electrochemical meta-C-H functionalization, achieving remote C-H bromination in an undivided cell under ligand- and electrolyte-free conditions. Notably, pyrazolylarenes were selectively brominated at the benzenoid moiety rather than the electron-rich pyrazole ring for the first time. Mechanistic studies suggested the formation of a ruthenacycle followed by a ligand-to-ligand hydrogen transfer (LLHT) process.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

Argha Saha et al.

Summary: The Fujiwara-Moritani reaction has made a significant contribution to contemporary C-H activation protocols. By establishing a photoredox catalytic system, the regioselective Fujiwara-Moritani reaction can be achieved through visible light without the need for silver salts and thermal energy. This sustainable protocol has importance in synthesizing natural products, chiral molecules, drugs, and diversifying functionalizations.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Empirical Guidelines for the Development of Remote Directing Templates through Quantitative and Experimental Analyses

Nelson Y. S. Lam et al.

Summary: This study summarizes key factors for achieving high selectivity at defined aryl positions by analyzing 119 structurally unique remote DTs, which are experimentally corroborated through the development of new aliphatic meta and para-selective DTs for electronically unbiased arenes. These empirical rules, summarizing key distance and geometric factors, are expected to be useful tools for the future development of site-selective arene C-H activation and other reactions relying on covalent/noncovalent DT-mediated remote regioselection.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

Philip Boehm et al.

Summary: An efficient palladium-catalyzed iodination method has been developed for the synthesis of iodides from inexpensive and abundant aryl and vinyl carboxylic acids, including complex drug-like scaffolds. The unique mechanism involves C-P reductive elimination to form Xantphos phosphonium chloride, which then initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Site-Selective C-H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent

Tao Zhang et al.

Summary: The site-selective C-H iodination of electron-rich phenols was achieved through a palladium(II)-catalyzed reaction using 4-iodo-3-nitroanisole as the mild iodinating reagent. The reaction exhibited excellent substrate selectivity and functional group tolerance in a range of electron-rich phenol derivatives, suggesting it as a potentially useful method for challenging substrates.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Palladium-catalyzed meta-C-H bond iodination of arenes with I2

Min Liu et al.

CHINESE CHEMICAL LETTERS (2020)

Article Chemistry, Multidisciplinary

Synthesis of Chiral β-Lactams by Pd-Catalyzed Enantioselective Amidation of Methylene C(sp3)-H Bonds

Tao Zhou et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach

Guangrong Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Synthesis of meta-Substituted Anilines via Copper-Catalyzed [1,3]-Methoxy Rearrangement

Itaru Nakamura et al.

ORGANIC LETTERS (2020)

Article Chemistry, Physical

Boron Recycling in the Metal-Free Transfer C-H Borylation of Terminal Alkynes and Heteroarenes

Vincent Desrosiers et al.

ACS CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Noncovalent Interaction in Transition Metal-Catalyzed Selective C-H Activation

Liao Gang et al.

ACTA CHIMICA SINICA (2020)

Review Chemistry, Multidisciplinary

Catalytic Isofunctional Reactions-Expanding the Repertoire of Shuttle and Metathesis Reactions

Benjamin N. Bhawal et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage

Chao Fan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Carboxylate-Assisted Oxidative Addition to Aminoalkyl PdII Complexes: C(sp3)-H Arylation of Alkylamines by Distinct PdII/PdIV Pathway

William G. Whitehurst et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Palladium/Norbornene Cooperative Catalysis

Jianchun Wang et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis

Etienne Rochette et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation

Madalina T. Mihai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions

Jose R. Montero Bastidas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Carboxy Group as a Remote and Selective Chelating Group for C-H Activation of Arenes

Shangda Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Accessing Remote meta- and para-C(sp(2))-H Bonds with Covalently Attached Directing Groups

Aniruddha Dey et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

3d Transition Metals for C-H Activation

Parthasarathy Gandeepan et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes

Hua-Jin Xu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Arene-Limited Nondirected C-H Activation of Arenes

Philipp Wedi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Ligand-promoted ruthenium-catalyzed meta C-H chlorination of arenes using N-chloro-2,10-camphorsultam

Zhoulong Fan et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Organic

Regioselective Transition-Metal-Catalyzed C-H Functionalization of Anilines

Jamie A. Leitch et al.

SYNTHESIS-STUTTGART (2018)

Article Chemistry, Organic

Concept of Ir-catalyzed C-H bond activation/borylation by noncovalent interaction

Chabush Haldar et al.

TETRAHEDRON LETTERS (2018)

Article Chemistry, Organic

Highly meta-selective halogenation of 2-phenylpyridine with a ruthenium(I) catalyst

Ganapam Manohar Reddy et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

Article Chemistry, Multidisciplinary

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis

Maximiliano De La Higuera Macias et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives

Rui-Jie Mi et al.

ORGANIC LETTERS (2018)

Article Chemistry, Multidisciplinary

Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

Ranjana Bisht et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis

Shogo Okumura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Mild Palladium Catalyzed ortho C-H Bond Functionalizations of Aniline Derivatives

Orsolya Tischler et al.

CHEMICAL RECORD (2017)

Article Multidisciplinary Sciences

Ligand-accelerated non-directed C-H functionalization of arenes

Peng Wang et al.

NATURE (2017)

Article Chemistry, Physical

Copper-Catalyzed Hydrogen/Iodine Exchange in Terminal and 1-Iodoalkynes

Ryan Chung et al.

ACS CATALYSIS (2017)

Review Chemistry, Multidisciplinary

Ruthenium-catalysed σ-activation for remote meta-selective C-H functionalisation

Jamie A. Leitch et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed para-Selective C-H Alkylation of Aniline Derivatives

Jamie A. Leitch et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Activation of Remote meta-C-H Bonds in Arenes with Tethered Alcohols: A Salicylonitrile Template

Lanlan Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed C-H Amination: Scope, Mechanism, and Applications

Yoonsu Park et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation

Marc Font et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Rhodium-Catalyzed meta-C-H Functionalization of Arenes

Milan Bera et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides

Gang Li et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

meta-C-H Bromination on Purine Bases by Heterogeneous Ruthenium Catalysis

Svenja Warratz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

The Evolution of Pd0/PdIICatalyzed Aromatic Fluorination

Aaron C. Sather et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Multidisciplinary

Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon-Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group

Yinlin Shao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Reaching the south: metal-catalyzed transformation of the aromatic para-position

Aniruddha Dey et al.

CHEMICAL COMMUNICATIONS (2016)

Review Chemistry, Multidisciplinary

Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation

David A. Petrone et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Carboxylic Acids as Directing Groups for C-H Bond Functionalization

Martin Pichette Drapeau et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Multidisciplinary

KOtBu-Initiated Aryl C-H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds

Qinqin Shi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Ligand-Promoted meta-C-H Amination and Alkynylation

Peng Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Peng Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Ligand Promoted meta-C-H Chlorination of Anilines and Phenols

Hang Shi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts

Holly J. Davis et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Multidisciplinary Sciences

Pd(II)-catalysed meta-C-H functionalizations of benzoic acid derivatives

Shangda Li et al.

NATURE COMMUNICATIONS (2016)

Article Chemistry, Physical

Catalytic Transfer Functionalization through Shuttle Catalysis

Benjamin N. Bhawal et al.

ACS CATALYSIS (2016)

Review Chemistry, Multidisciplinary

Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds

Olafs Daugulis et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Review Chemistry, Multidisciplinary

Recent Advances on Transition-Metal-Catalyzed Halogenation of Unactivated C-H Bonds

Liao Gang et al.

ACTA CHIMICA SINICA (2015)

Article Chemistry, Multidisciplinary

Directed meta-Selective Bromination of Arenes with Ruthenium Catalysts

Qingzhen Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed meta-Selective C-H Bromination

Christopher J. Teskey et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

N-Acyl Amino Acid Ligands for Ruthenium(II)-Catalyzed meta-C-H tert-Alkylation with Removable Auxiliaries

Jie Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Review Chemistry, Organic

Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups

Zhengkai Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

Review Chemistry, Multidisciplinary

The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations

Simon A. Girard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Multidisciplinary Sciences

Conformation-induced remote meta-C-H activation of amines

Ri-Yuan Tang et al.

NATURE (2014)

Article Multidisciplinary Sciences

Room-temperature enantioselective C-H iodination via kinetic resolution

Ling Chu et al.

SCIENCE (2014)

Article Chemistry, Multidisciplinary

Copper-catalyzed ortho-halogenation of protected anilines

Beatriz Urones et al.

CHEMICAL COMMUNICATIONS (2013)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed C-H Iodination Using Molecular I2 as the Sole Oxidant

Xiao-Chen Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Chemistry, Multidisciplinary

Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions

Keary M. Engle et al.

ACCOUNTS OF CHEMICAL RESEARCH (2012)

Review Chemistry, Multidisciplinary

From C(sp(2))-H to C(sp(3))-H: systematic studies on transition metal-catalyzed oxidative C-C formation

Bi-Jie Li et al.

CHEMICAL SOCIETY REVIEWS (2012)

Review Chemistry, Multidisciplinary

C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation

Guoyong Song et al.

CHEMICAL SOCIETY REVIEWS (2012)

Article Chemistry, Multidisciplinary

High-Yielding, Versatile, and Practical [Rh(III)Cp*]-Catalyzed Ortho Bromination and Iodination of Arenes

Nils Schroeder et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Multidisciplinary Sciences

Activation of remote meta-C-H bonds assisted by an end-on template

Dasheng Leow et al.

NATURE (2012)

Article Chemistry, Multidisciplinary

A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives

Claire-Lise Ciana et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds

Charles S. Yeung et al.

CHEMICAL REVIEWS (2011)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed C-H Aminations of Anilides with N-Fluorobenzenesulfonimide

Kai Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Applied

Selective C3-C3 Oxidative Cross-Coupling between Unactivated Anilines and Indoles

Linfei Wang et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions

Thomas W. Lyons et al.

CHEMICAL REVIEWS (2010)

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)

Article Multidisciplinary Sciences

A Meta-Selective Copper-Catalyzed C-H Bond Arylation

Robert J. Phipps et al.

SCIENCE (2009)

Article Chemistry, Multidisciplinary

Highly selective C-H functionalization/halogenation of acetanilide

Xiaobing Wan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

A highly selective catalytic method for the oxidative functionalization of C-H bonds

AR Dick et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Reductive elimination of aryl halides from palladium(II)

AH Roy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)