☆ 4.4 Article

Ritter reaction for the synthesis of picolinamides

TETRAHEDRON (2022)

Related references

Note: Only part of the references are listed.

Article Chemistry, Organic

Regioselective 1,2-carbosulfenylation of unactivated alkenes via directed nickel catalysis

Lin Zhu et al.

Summary: In this study, a bidentate directing group-assisted Ni-catalyzed three component 1,2-carbosulfenylation reaction was reported, which allows for the transformation of unactivated alkenes using aryl/alkenylboronic acids and disulfide electrophiles. The reaction showed high levels of chemo- and regioselectivity and could introduce a wide range of aryl groups and sulfur moieties into homoallylic amines. Notably, it also enabled the synthesis of α,gamma-dibranched thiolamines with high diastereoselectivity and enantioselectivity.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Allene C(sp2)-H Activation and Alkenylation Catalyzed by Palladium

Benedikt S. Schreib et al.

Summary: In this study, a Pd-catalyzed C-H alkenylation reaction of electronically unbiased allenes was reported, providing penta-1,2,4-triene products in up to 94% yield. The use of picolinamide directing group enabled the formation of allenyl-palladacycles, which subsequently participated in a turnover-limiting Heck-type reaction with electron-deficient alkene coupling partners. Additionally, picolinamide N,O-acetals were introduced as readily removable auxiliaries for C-H activation reactions, facilitating the efficient alkenylation of allenyl carbinol derivatives while maintaining the reactivity of the products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Chemistry, Organic

Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines

Lei Zhao et al.

Summary: This report describes an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides using a Ni(II) catalyst. By utilizing cleavable bidentate quinolinamide, the reaction enables olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol, providing rapid access to branched aliphatic amines with high diastereoselectivities.

ORGANIC LETTERS (2021)

Add to Collection

Article Multidisciplinary Sciences

Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes

Leipeng Xie et al.

Summary: The authors presented a method to add aryl and amino groups to alkenes regio- and diastereoselectively via nickel catalysis and a removable directing group. This method enables high levels of regio-, chemo- and diastereocontrol, and is compatible with broad substrate scope and high functional group tolerance. The utility of this method in site-selective modification of pharmaceutical agents has been demonstrated.

NATURE COMMUNICATIONS (2021)

Add to Collection

Article Multidisciplinary Sciences

γ-Selective C(sp3)-H amination via controlled migratory hydroamination

Changseok Lee et al.

Summary: A new method has been developed for remote functionalization of alkenes at unreactive positions, achieving gamma-C(sp(3))-H functionalization through controlled alkene transposition, which has been a longstanding challenge. By tuning olefin isomerization and migratory hydroamination, gamma-selective amination can be achieved via stabilization of a 6-membered nickellacycle and subsequent interception by an aminating reagent. This approach enables late-stage access to value-added products and has been further extended to delta-selective amination by employing picolinamide-coupled alkene substrates.

NATURE COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Sovan Biswas et al.

Summary: Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. The protocol allows for the preparation of substituted analogues with ease, and the use of a Cu catalyst in the Ullmann-Goldberg reaction helps avoid interference from off-cycle Pd catalyst scavenging.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Regioselective nickel-catalyzed dicarbofunctionalization of unactivated alkenes enabled by picolinamide auxiliary

Shenghao Wang et al.

Summary: The research presented here developed a novel catalytic system for regioselective dicarbofunctionalization of homoallylic amines. By activating cost-effective Ni(II) precatalyst with arylboronic acids, selective diarylation and arylalkylation of unactivated alkenes was achieved.

CELL REPORTS PHYSICAL SCIENCE (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Tropylium-promoted Ritter reactions

Son H. Doan et al.

Summary: The newly developed method utilizing salts of the tropylium ion to promote the Ritter reaction shows good performance on various alcohol and nitrile substrates, yielding products in good to excellent yields. This reaction protocol is compatible with microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

CHEMICAL COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium-Catalyzed C-H Alkynylation of Unactivated Alkenes

Benedikt S. Schreib et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Bidentate Directing Groups: An Efficient Tool in C-H Bond Functionalization Chemistry for the Expedient Construction of C-C Bonds

Supriya Rej et al.

CHEMICAL REVIEWS (2020)

Add to Collection

Article Chemistry, Organic

Construction of Cyclophane-Braced Peptide Macrocycles via Palladium-Catalyzed Picolinamide-Directed Intramolecular C(sp2)-H Arylation

Boyang Han et al.

ORGANIC LETTERS (2020)

Add to Collection

Article Chemistry, Multidisciplinary

NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes

Jinwon Jeon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Article Multidisciplinary Sciences

Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation

Hui-Qi Ni et al.

NATURE COMMUNICATIONS (2020)

Add to Collection

Article Chemistry, Organic

Synthesis and Prediction of the Ubiquinol-cytochrome c Reductase Inhibitory Activity of 3,4-Dihydroisoquinolines and 2-Azaspiro[4.5]decanes (Spiropyrrolines)

Anna N. Perevoshchikova et al.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes

Benedikt S. Schreib et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C-H Arylation

Bo Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Add to Collection

Article Chemistry, Organic

Pd-Mediated γ-C(sp3)-H Bond Activation in Ammonia-Ugi 4-CR Adducts by Using Picolinamide as Directing Group

Diego Aleman-Ponce de Leon et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary

Zhen Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Organic

Directed C-H Functionalization Reactions with a Picolinamide Directing Group: Ni-Catalyzed Cleavage and Byproduct Recycling

Sovan Biswas et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl

Joseph Derosa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Add to Collection

Article Chemistry, Multidisciplinary

An Enantioselective Bidentate Auxiliary Directed Palladium-Catalyzed Benzylic C-H Arylation of Amines Using a BINOL Phosphate Ligand

Hao Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

Zhen Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Add to Collection

Article Chemistry, Organic

The reductive cleavage of picolinic amides

Daniel H. O'Donovan et al.

TETRAHEDRON LETTERS (2016)

Add to Collection

Review Chemistry, Multidisciplinary

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

Olafs Daugulis et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Add to Collection

Article Chemistry, Organic

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

Enrico T. Nadres et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Heterocycle Synthesis via Direct C-H/N-H Coupling

Enrico T. Nadres et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

Masashi Hayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Add to Collection

Article Chemistry, Organic

Improved Protocol for Indoline Synthesis via Palladium-Catalyzed Intramolecular C(sp2)-H Amination

Gang He et al.

ORGANIC LETTERS (2012)

Add to Collection

Article Chemistry, Organic

Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction

Palani Theerthagiri et al.

TETRAHEDRON LETTERS (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Highly regloselective arylation of Sp3 C-H bonds catalyzed by palladium acetate

VG Zaitsev et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Add to Collection

© Peeref 2019-2024. All rights reserved.