☆ 4.7 Article

Palladium-catalyzed Atroposelective Interannular C-H Arylation of Biaryl Aldehydes with Aryl Iodides Enabled by a Transient Directing Group Strategy

ADVANCED SYNTHESIS & CATALYSIS (2022)

Related references

Note: Only part of the references are listed.

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)

Add to Collection

Article Chemistry, Multidisciplinary

Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy

Yujian Mao et al.

Summary: Methyl groups are commonly found in bioactive molecules, and site-specific methylation has become an important strategy for their structural functionalization. In this study, a highly regioselective peri- and ortho-C-H methylation of 1-naphthaldehyde was achieved using a transient ligand strategy, leading to the synthesis of various methyl-substituted naphthalene frameworks. The mechanism of peri-methylation and ortho-methylation was investigated, providing insights into the control factors and energetically favorable pathways.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group

Joe Higham et al.

Summary: Transient directing groups (TDGs) combined with copper have been used for efficient C-H functionalization without additional steps for directing group introduction and removal. This method demonstrates high regioselectivity in the beta-C(sp(2))-H sulfonylation and gamma-(peri)-sulfonylation reactions of benzaldehydes and achieves through the use of catalytic beta-alanine and sulfinate salts, with copper fluoride serving as both the copper source and oxidant.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

PdII-Catalyzed Site-selectiveβ- andγ-C(sp3)-H Arylation of PrimaryAldehydes Controlled by Transient Directing Groups

Yi-Hao Li et al.

Summary: Pd(II)-catalyzed site-selective beta- and gamma-C(sp3)-H arylation of primary aldehydes is achieved by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are crucial for the observed reactivity. By minimizing the loading of acid additives, the ligand effect is enhanced to achieve high reactivities of the challenging primary aldehyde substrates. Site selectivity can be switched by changing the bite angle of TDG to match the desired palladacycle size, as supported by experimental and computational investigations.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Organic

Pd(II)-Catalyzed Transient Directing Group-Assisted Regioselective Diverse C4-H Functionalizations of Indoles

Anurag Singh et al.

Summary: A novel method for achieving C4 chlorination/bromination or acetoxylation of indoles by transient directing group (TDG) assistance has been disclosed in this study. The use of inexpensive CuX2 as the halide source highlights the practicality of this approach.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Pd-Catalyzed β-C-H Arylation of Aldehydes and Ketones Based on a Transient Directing Group

Liang-Fei Wu et al.

Summary: A novel method utilizing 2-amino-N,N'-diisopropylsuccinamide as a transient directing group was developed for the direct Pd-catalyzed beta-C-H arylation of aldehydes and ketones. This method demonstrated good versatility in functionalizing unactivated beta-C-H bonds of both aliphatic and aromatic aldehydes and ketones, as well as o-methylbenzaldehydes.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective palladaelectro-catalyzed C-H olefinations and allylations for N-C axial chirality

Uttam Dhawa et al.

Summary: Enantioselective palladaelectro-catalyzed C-H alkenylations and allylations were achieved using easily-accessible amino acids as transient directing groups, leading to highly enantiomerically-enriched products. The synthetic utility of the strategy was demonstrated with various alkenes, while the versatility of the approach was reflected by atroposelective C-H allylations. Computational studies provided insights into the facile C-H activation by a seven-membered palladacycle.

CHEMICAL SCIENCE (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy

Chaolumen Bai et al.

Summary: This study reports the regioselective cross-coupling reactions in the o-methyl benzaldehyde frameworks using palladium catalysis, K2S2O8 or [F+] reagents as oxidants, and unactivated arenes as substrates/solvents. The regiospecificity is controlled by [5,6]-fused or [6,5]-fused palladacycle intermediates formed from Pd-chelation with specific transient directing groups and C-H activations.

CHEMICAL COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Organic

Pd(ii)-Catalyzed enantioconvergent twofold C-H annulation to access atropisomeric aldehydes: a platform for diversity-oriented-synthesis

Jitan Zhang et al.

Summary: A novel Pd(II)-catalyzed reaction for the synthesis of axially chiral aldehydes with high yields and excellent enantioselectivity has been developed. This method allows for diverse late-stage transformations to access structurally diverse compounds.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of Axially Chiral Styrenes through Pd-Catalyzed Asymmetric C-H Olefination Enabled by an Amino Amide Transient Directing Group

Hong Song et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Article Chemistry, Multidisciplinary

PdII-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group

Li-Jun Xiao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective Pallada-Electrocatalyzed C-H Activation by Transient Directing Groups: Expedient Access to Helicenes

Uttam Dhawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Enantioselective C-H Functionalization via Chiral Transient Directing Group Strategies

Gang Liao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Article Chemistry, Organic

Pd-Catalyzed C(sp3)-H Biarylation via Transient Directing Group Strategy

Mingruo Ding et al.

ORGANIC LETTERS (2020)

Add to Collection

Article Chemistry, Physical

Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics by Pd-Catalyzed C-H Alkynylation

Shuo Zhang et al.

ACS CATALYSIS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Transient Ligand-Enabled Transition Metal-Catalyzed C-H Functionalization

Ben Niu et al.

CHEMSUSCHEM (2019)

Add to Collection

Article Chemistry, Organic

Asymmetric Total Synthesis of TAN-1085 Facilitated by Pd-Catalyzed Atroposelective C-H Olefination

Jun Fan et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Organic

Rhodium(III)-Catalyzed Intramolecular Olefin Hydroarylation of Aromatic Aldehydes Using a Transient Directing Group

Zhe Guan et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Organic

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

Feng Li et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Atroposelective C-H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls

Qiang Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Add to Collection

Article Chemistry, Organic

Construction of N-C Axial Chirality through Atroposelective C-H Olefination of N-Arylindoles by Palladium/Amino Acid Cooperative Catalysis

Jitan Zhang et al.

ORGANIC LETTERS (2019)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Pd-Catalyzed Atroposelective C-H Allylation and Alkenylation: Access to Enantioenriched Atropisomers Featuring Pentatomic Heteroaromatics

Hao-Ming Chen et al.

ORGANOMETALLICS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Catalysis with Palladium Complexes Photoexcited by Visible Light

Padon Chuentragool et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Organic

A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids

Rickki L. Connelly et al.

ORGANIC LETTERS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Recent advances in the synthesis of axially chiral biaryls via transition metal-catalysed asymmetric C-H functionalization

Gang Liao et al.

CHEMICAL COMMUNICATIONS (2019)

Add to Collection

Article Chemistry, Organic

Assembly of Diverse Spirocyclic Pyrrolidines via Transient Directing Group Enabled Ortho-C(sp(2))-H Alkylation of Benzaldehydes

Feng Li et al.

ORGANIC LETTERS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

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

Gang Liao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium-catalyzed enantioselective C(sp(2))-H arylation of ferrocenyl ketones enabled by a chiral transient directing group

Jiancong Xu et al.

CHEMICAL COMMUNICATIONS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium-Catalyzed ortho C-H Arylation of Benzaldehydes Using ortho-Sulfinyl Aniline as Transient Auxiliary

Delong Mu et al.

CHEMISTRY-AN ASIAN JOURNAL (2018)

Add to Collection

Article Chemistry, Organic

Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp2)-H Arylation

Meng Yao Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Controlling Pd(IV) reductive elimination pathways enables Pd(II)-catalysed enantioselective C(sp(3))-H fluorination

Hojoon Park et al.

NATURE CHEMISTRY (2018)

Add to Collection

Article Chemistry, Organic

Direct Dehydrogenative Arylation of Benzaldehydes with Arenes Using Transient Directing Groups

Da-Yu Wang et al.

ORGANIC LETTERS (2018)

Add to Collection

Review Chemistry, Multidisciplinary

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

Parthasarathy Gandeepan et al.

CHEM (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Pd-Catalyzed Atroposelective C-H Allylation through β-O Elimination: Diverse Synthesis of Axially Chiral Biaryls

Gang Liao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection

Article Chemistry, Multidisciplinary

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

Xi-Hai Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Add to Collection

Article Chemistry, Physical

Enantioselective Synthesis of Indole-Based Biaryl Atropisomers via Palladium-Catalyzed Dynamic Kinetic Intramolecular C-H Cyclization

Congfa He et al.

ACS CATALYSIS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Atroposelective Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Asymmetric C-H Olefination Enabled by a Transient Chiral Auxiliary

Qi-Jun Yao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Multidisciplinary Sciences

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

Fang-Lin Zhang et al.

SCIENCE (2016)

Add to Collection

Article Chemistry, Multidisciplinary

On the Interpretation of Deuterium Kinetic Isotope Effects in C?H Bond Functionalizations by Transition-Metal Complexes

Eric M. Simmons et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

© Peeref 2019-2024. All rights reserved.