Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation

Scalable, Stereocontrolled Formal Syntheses of (+)-Isoschizandrin and (+)-Steganone: Development and Applications of Palladium(II)-Catalyzed Atroposelective C−H Alkynylation

(2018) Gang Liao et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Transient-Ligand-Enabled ortho -Arylation of Five-Membered Heterocycles: Facile Access to Mechanochromic Materials

(2018) Bijin Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Palladium-catalyzed site-selective arylation of aliphatic ketones enabled by a transient ligand

(2018) Lei Pan et al.   CHEMICAL COMMUNICATIONS

Palladium-catalyzed enantioselective C(sp2)–H arylation of ferrocenyl ketones enabled by a chiral transient directing group

(2018) Jiancong Xu et al.   CHEMICAL COMMUNICATIONS

Access to the meta position of arenes through transition metal catalysed C–H bond functionalisation: a focus on metals other than palladium

(2018) Madalina T. Mihai et al.   CHEMICAL SOCIETY REVIEWS

Aromatic Aminocatalysis

(2018) Jian Lv et al.   Chemistry-An Asian Journal

Rh-catalyzed Transient Directing Group Promoted C-H Amidation of Benzaldehydes Utilizing Dioxazolones

(2018) Xiaoyang Wang et al.   CHINESE JOURNAL OF CHEMISTRY

Pd-Catalyzed, ortho C–H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups

(2018) Xiao-Yang Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Direct Dehydrogenative Arylation of Benzaldehydes with Arenes Using Transient Directing Groups

(2018) Da-Yu Wang et al.   ORGANIC LETTERS

Ruthenium-Catalyzed Ortho C(sp2)–H Amidation of Benzaldehydes with Organic Azides

(2018) Omer Rasheed   SYNLETT

Rh(III)-catalyzed synthesis of unsymmetrical acridines from aldehydes and azides using transient directing strategy in biomass-derived γ-valerolactone

(2018) Jun Shen et al.   SYNTHETIC COMMUNICATIONS

Direct synthesis of anthracenes from o -tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp 3 C H arylation and electrophilic aromatic cyclization

(2018) Hyojin Park et al.   TETRAHEDRON

sp3 C–H activation via exo-type directing groups

(2018) Yan Xu et al.   Chemical Science

Pd(ii)-catalyzed synthesis of bifunctionalized carboranes via cage B–H activation of 1-CH2NH2-o-carboranes

(2018) Xiaolei Zhang et al.   Chemical Science

The stabilizing effect of the transient imine directing group in the Pd(ii)-catalyzed C(sp3)–H arylation of free primary amines

(2018) Xiao-Xiao Hu et al.   Organic Chemistry Frontiers

Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis

(2018) Parthasarathy Gandeepan et al.   Chem

Iridium-Catalyzed ortho-C(sp2)–H Amidation of Benzaldehydes with Organic Azides

(2017) Delong Mu et al.   JOURNAL OF ORGANIC CHEMISTRY

Highly Versatile β-C(sp3)–H Iodination of Ketones Using a Practical Auxiliary

(2017) Ru-Yi Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Pd(II)-Catalyzed Enantioselective C(sp3)–H Borylation

(2017) Jian He et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Selective Catalytic B–H Arylation of o-Carboranyl Aldehydes by a Transient Directing Strategy

(2017) Xiaolei Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Diverse ortho-C(sp2)–H Functionalization of Benzaldehydes Using Transient Directing Groups

(2017) Xi-Hai Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Pd-Catalyzed Direct ortho-C–H Arylation of Aromatic Ketones Enabled by a Transient Directing Group

(2017) Jiancong Xu et al.   ORGANIC LETTERS

Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C–H Functionalizations Using a Transient Directing Group

(2017) Xiao-Yang Chen et al.   ORGANIC LETTERS

Pd-Catalyzed Ortho C–H Hydroxylation of Benzaldehydes Using a Transient Directing Group

(2017) Xiao-Yang Chen et al.   ORGANIC LETTERS

Assembly of Diverse Spirocyclic Pyrrolidines via Transient Directing Group Enabled Ortho-C(sp2)–H Alkylation of Benzaldehydes

(2017) Feng Li et al.   ORGANIC LETTERS

Single operation palladium catalysed C(sp3)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups

(2017) S. St John-Campbell et al.   Chemical Science

Methylene C(sp3)–H Arylation of Aliphatic Ketones Using a Transient Directing Group

(2017) Kai Hong et al.   ACS Catalysis

Palladium catalyzed C(sp3)–H acetoxylation of aliphatic primary amines to γ-amino alcohol derivatives

(2017) Kang Chen et al.   Organic Chemistry Frontiers

Ligand-Accelerated Direct C−H Arylation of BINOL: A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs

(2016) Jin-Fei Yang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ligand-Enabled Arylation of γ-C−H Bonds

(2016) Suhua Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic C(sp3)−H Arylation of Free Primary Amines with anexoDirecting Group Generated In Situ

(2016) Yan Xu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Buttressing Salicylaldehydes: A Multipurpose Directing Group for C(sp3)−H Bond Activation

(2016) Akira Yada et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Palladium-Catalyzed Transformations of Alkyl C–H Bonds

(2016) Jian He et al.   CHEMICAL REVIEWS

Ir-Catalyzed C−H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group

(2016) Yun-Fei Zhang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Bridging C−H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group

(2016) Martin Berger et al.   CHEMISTRY-A EUROPEAN JOURNAL

Catalytic C–H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

(2016) Ke Yang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Pd-Catalyzed γ-C(sp3)–H Arylation of Free Amines Using a Transient Directing Group

(2016) Yongwei Wu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-catalysed transannular C–H functionalization of alicyclic amines

(2016) Joseph J. Topczewski et al.   NATURE

Palladium catalysed meta-C–H functionalization reactions

(2016) Aniruddha Dey et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Advances in the development of catalytic tethering directing groups for C–H functionalization reactions

(2016) Huan Sun et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp3)–H Bonds

(2016) Fei Ma et al.   ORGANIC LETTERS

Functionalization of C(sp3)-H bonds using a transient directing group

(2016) F.-L. Zhang et al.   SCIENCE

Ligand-accelerated enantioselective methylene C(sp3)–H bond activation

(2016) Gang Chen et al.   SCIENCE

The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols

(2016) Brian J. Knight et al.   Chemical Science

β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst

(2016) Jing Peng et al.   Chemical Science

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

(2015) Olafs Daugulis et al.   ACCOUNTS OF CHEMICAL RESEARCH

Catalytic Intramolecular Ketone Alkylation with Olefins by Dual Activation

(2015) Hee Nam Lim et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ligand-Enabled Catalytic CH Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway

(2015) Chuan He et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Bifunctional Ligand-Assisted Catalytic Ketone α-Alkenylation with Internal Alkynes: Controlled Synthesis of Enones and Mechanistic Studies

(2015) Fanyang Mo et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

(2015) Jie Li et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Remote para-C–H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly

(2015) Sukdev Bag et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

(2015) Rajagopal Santhoshkumar et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A steric tethering approach enables palladium-catalysed C–H activation of primary amino alcohols

(2015) Jonas Calleja et al.   Nature Chemistry

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

(2015) Zhengkai Chen et al.   Organic Chemistry Frontiers

Directing Remote Meta-C–H Functionalization with Cleavable Auxiliaries

(2015) Christopher G. Frost et al.   ACS Central Science

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

(2014) Suman De Sarkar et al.   ADVANCED SYNTHESIS & CATALYSIS

Aldehyde-Assisted Ruthenium(II)-Catalyzed CH Oxygenations

(2014) Fanzhi Yang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Arene C–H functionalisation using a removable/modifiable or a traceless directing group strategy

(2014) Fengzhi Zhang et al.   CHEMICAL SOCIETY REVIEWS

Palladium-catalysed C–H activation of aliphatic amines to give strained nitrogen heterocycles

(2014) Andrew McNally et al.   NATURE

Regio- and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)–H Arylation

(2014) Dominic P. Affron et al.   ORGANIC LETTERS

Regioselective ketone  -alkylation with simple olefins via dual activation

(2014) F. Mo et al.   SCIENCE

Recent advances in directed C–H functionalizations using monodentate nitrogen-based directing groups

(2014) Min Zhang et al.   Organic Chemistry Frontiers

Palladium-Catalyzed Direct Functionalization of 2-Aminobutanoic Acid Derivatives: Application of a Convenient and Versatile Auxiliary

(2013) Mengyang Fan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)H Bonds

(2013) Gang He et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Mild Rhodium(III)-Catalyzed Direct CH Allylation of Arenes with Allyl Carbonates

(2013) Honggen Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic Functionalization of C(sp2)H and C(sp3)H Bonds by Using Bidentate Directing Groups

(2013) Guy Rouquet et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium-Catalyzed Selective Aerobic Oxidativeortho-Alkenylation of Substituted Phenols with Alkenes through C-H Bond Activation

(2013) Mallu Chenna Reddy et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C–H Bonds

(2013) Enrico T. Nadres et al.   JOURNAL OF ORGANIC CHEMISTRY

Developing Ligands for Palladium(II)-Catalyzed C–H Functionalization: Intimate Dialogue between Ligand and Substrate

(2013) Keary M. Engle et al.   JOURNAL OF ORGANIC CHEMISTRY

Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group

(2013) Hyun Jin Kim et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rhodium(III)-Amine Dual Catalysis for the Oxidative Coupling of Aldehydes by Directed C–H Activation: Synthesis of Phthalides

(2013) Peng Wen Tan et al.   ORGANIC LETTERS

Regioselective Synthesis of 4-Substituted Indoles via C–H Activation: A Ruthenium Catalyzed Novel Directing Group Strategy

(2013) Veeranjaneyulu Lanke et al.   ORGANIC LETTERS

Pd(ii)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a removable directing group: efficient synthesis of alkyl ethers

(2013) Fa-Jie Chen et al.   Chemical Science

Pd-Catalyzed CH Oxygenation with TFA/TFAA: Expedient Access to Oxygen-Containing Heterocycles and Late-Stage Drug Modification

(2012) Gang Shan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

(2012) Junichiro Yamaguchi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cooperative Catalysis Approach to Intramolecular Hydroacylation

(2012) Evgeny V. Beletskiy et al.   JOURNAL OF ORGANIC CHEMISTRY

Highly Regio- and Stereoselective Ruthenium(II)-Catalyzed Direct ortho-Alkenylation of Aromatic and Heteroaromatic Aldehydes with Activated Alkenes under Open Atmosphere

(2012) Kishor Padala et al.   ORGANIC LETTERS

Adding Aliphatic C-H Bond Oxidations to Synthesis

(2012) M. C. White   SCIENCE

Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)–H γ-arylation of amino acid derivatives

(2012) Nuria Rodríguez et al.   Chemical Science

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

(2011) Keary M. Engle et al.   ACCOUNTS OF CHEMICAL RESEARCH

Synthesis of a Palladium(IV) Complex by Oxidative Addition of an Aryl Halide to Palladium(II) and Its Use as Precatalyst in a CC Coupling Reaction

(2011) José Vicente et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation

(2011) Josep Cornella et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

If CH Bonds Could Talk: Selective CH Bond Oxidation

(2011) Timothy Newhouse et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system

(2011) Nicolas R. Vautravers et al.   CHEMICAL COMMUNICATIONS

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

(2011) Lutz Ackermann   CHEMICAL REVIEWS

Transition metal-catalyzed arylation of unactivated C(sp3)–H bonds

(2011) Olivier Baudoin   CHEMICAL SOCIETY REVIEWS

Towards mild metal-catalyzed C–H bond activation

(2011) Joanna Wencel-Delord et al.   CHEMICAL SOCIETY REVIEWS

Overview of the Mechanistic Work on the Concerted Metallation–Deprotonation Pathway

(2010) David Lapointe et al.   CHEMISTRY LETTERS

Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2and sp3Carbon−Hydrogen Bonds

(2010) Dmitry Shabashov et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Asymmetric catalysis with chiral primary amine-based organocatalysts

(2009) Li-Wen Xu et al.   CHEMICAL COMMUNICATIONS

Mechanisms of C–H bond activation: rich synergy between computation and experiment

(2009) Youcef Boutadla et al.   DALTON TRANSACTIONS

Pd(0)/PR3-Catalyzed Intermolecular Arylation of sp3C−H Bonds

(2009) Masayuki Wasa et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The advent and development of organocatalysis

(2008) David W. C. MacMillan   NATURE