☆ 4.8 Article

Uncanonical Semireduction of Quinolines and Isoquinolines via Regioselective HAT-Promoted Hydrosilylation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Won Seok Ham et al.

Summary: This study describes a synthetic platform for site-selective C-H functionalization, which can be transformed into various amine products in situ. The method is compatible with a broad range of pyrimidines with sensitive functional groups and can access complex aminopyrimidines with high selectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Physical

Light-Promoted Dearomative Cross-Coupling of Heteroarenium Salts and Aryl Iodides via Nickel Catalysis

Rajender Nallagonda et al.

Summary: Partially saturated nitrogen heterocycles are versatile building blocks that can be used to synthesize other nitrogen heterocycles. Coupling reactions between aryl iodides and pyridinium or other heteroarenium salts can produce a wide range of nitrogen heterocycle scaffolds. This method has high operability and good tolerance towards functional groups.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Borane-Catalyzed C3-Alkylation of Pyridines with Imines,Aldehydes, or Ketones as Electrophiles

Zhong Liu et al.

Summary: This study reports a borane-catalyzed tandem reaction method that achieves exclusively C3-selective alkylation of pyridines, providing a practical tool for late-stage functionalization of structurally complex pharmaceuticals bearing a pyridine moiety.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chemoselective (Hetero)Arene Electroreduction Enabled by RapidAlternating Polarity

Kyohei Hayashi et al.

Summary: This study reveals a simpler method for reduction reactions by altering the waveform of current delivery. The method can be performed in a protic solvent without the need for metal additives or stringent anhydrous conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Scaffold hopping by net photochemical carbon deletion of azaarenes

Jisoo Woo et al.

Summary: Discovery chemists use an iterative structural optimization method to identify purpose-tailored molecules, but the preparation of each candidate rarely matches their thought process. We report a method that allows chemists to directly switch between chemically distinct heteroaromatic scaffolds, addressing part of this problem.

SCIENCE (2022)

添加到收藏夹

Article Chemistry, Physical

KOtBu-Catalyzed 1,2-Silaboration of N-Heteroarenes to Access 2-Silyiheterocycles: A Cooperative Model for the Regioselectivity

Eunchan Jeong et al.

Summary: Reductive functionalization of N-heteroarenes is an important method for the synthesis of versatile heterocyclic compounds. In this study, the KOtBu-catalyzed 1,2-silaboration of N-heteroarenes was developed, leading to the formation of heterocyclic allylamines or enamines bearing a sp(3) C2-Si bond. The compounds were obtained either as N-acyl derivatives or as rearomatized 2-silyl-N-heteroarenes through one-pot procedures. A model of the six-membered ion-pair complex was proposed to explain the observed 1,2-regioselectivity, with KOtBu serving as an activating agent for the substrate and silylborane reagent.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Physical

Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2+2] cycloaddition/rearrangement reactions of quinolines with alkenes

Jiajia Ma et al.

Summary: Hybrid fused two-dimensional/three-dimensional rings are important in drugs due to their unique properties. However, their preparation often requires complex synthetic efforts and is inefficient. In this study, a cascade reaction mediated by energy transfer was developed to efficiently synthesize 2D/3D pyridine-fused ring systems.

NATURE CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

C3-Selective Trifluoromethylthiolation and Difluoromethylthiolation of Pyridines and Pyridine Drugs via Dihydropyridine Intermediates

Xin-Yue Zhou et al.

Summary: In this study, a method for functionalization of pyridines was reported, which exhibits high selectivity towards trifluoromethylthio and difluoromethylthio groups. The method can be used for late-stage functionalization of pyridine drugs, resulting in the generation of new drug candidates.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization

Peng Ji et al.

Summary: The synthesis of polycyclic structures bearing partially saturated (hetero)arenes is important. The authors develop a one-step method for selective dearomative functionalization of feedstock (hetero)arenes via organophotocatalysis. The method allows for rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.

NATURE COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies

Renyu Guo et al.

Summary: Photochemical dearomative cycloaddition is a useful strategy for rapidly generating molecular complexity, and intermolecular para-cycloadditions with stereo- and regiocontrol are rare. In this study, a method for achieving photochemical cycloaddition of quinolines and alkenes is presented, with an emphasis on generating sterically congested products and reacting highly substituted alkenes and allenes. The mechanistic details of the process, including reversible radical addition and selectivity-determining radical recombination, are investigated. The regio- and stereochemical outcome of the reaction is also rationalized.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible-Light Photocatalyzed peri-(3+2) Cycloadditions of Quinolines

Peter Bellotti et al.

Summary: This study presents a unique method for the one-step synthesis of aza-acenaphthenes through peri-(3 + 2) cycloaddition of simple quinolines with alkynes. A commercial iridium complex is used as a dual-function photosensitizer and photoredox catalyst, enabling a cyclization/rearomatization cascade. The method demonstrates excellent regio- and diastereoselectivity when applied to 8-substituted quinolines and phenanthrolines.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Visible-light induced dearomatization reactions

Yuan-Zheng Cheng et al.

Summary: This article presents an overview of visible-light-induced dearomatization reactions and their applications. These reactions provide a rapid and efficient way to synthesize complex molecules from simple aromatic compounds and have significant implications in the synthesis of natural products, medicinal chemistry, and materials science.

CHEMICAL SOCIETY REVIEWS (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

James Burrows et al.

Summary: This article presents a Birch reduction method that is simpler, safer, more efficient, and more environmentally friendly, for converting arenes into 1,4-cyclohexadienes. The method is easy to operate, cost-effective, and applicable to various chemical laboratories, making it a new technology with wide application prospects.

SCIENCE (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines

Arne Heusler et al.

Summary: A novel method for the synthesis of a broad variety of N-substituted 1,4- and 1,2-dihydropyridines using amine borane as a mild and selective reducing agent is reported, expanding the scope of dearomatization strategies.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Phosphorus-mediated sp2-sp3 couplings for C-H fluoroalkylation of azines

Xuan Zhang et al.

Summary: Fluoroalkyl groups have significant effects on the physical properties of pharmaceuticals and impact various metrics related to their pharmacokinetics and pharmacodynamics. The development of new fluoroalkylation reactions has led to the direct conversion of C-H bonds into complex C-CF2X groups in drug-like molecules. A novel approach using bench-stable fluoroalkylphosphines allows for the selective conversion of C-H bonds in pyridine building blocks and pharmaceuticals without the need for preinstalled functional groups or directing groups.

NATURE (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes

Jiajia Ma et al.

Summary: This study reveals a new energy transfer-mediated, highly selective dearomative cycloaddition reaction of bicyclic azaarenes with diverse alkenes. By bypassing the low reactivity and selectivity challenges of aromatic systems, this approach provides access to bridged polycycles that were previously inaccessible or required complex synthetic efforts. Computational studies using density functional theory help elucidate the mechanism and selectivity of this reaction.

SCIENCE (2021)

添加到收藏夹

Article Multidisciplinary Sciences

A radical approach for the selective C-H borylation of azines

Ji Hye Kim et al.

Summary: A new strategy for the borylation of azines has been developed, utilizing stable and inexpensive amine-borane reagents in conjunction with photocatalysis. This approach allows for selective borylation of nitrogen-containing aromatic heterocycles through the formation of highly reactive boryl radicals, providing an alternative tactic for sp(2) carbon-boron bond assembly. The strong nucleophilic character of the amine-boryl radicals enables predictable and site-selective carbon-boron bond formation in azine structures, leading to the preparation of borylated materials that are otherwise difficult to access.

NATURE (2021)

添加到收藏夹

Article Chemistry, Organic

Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins

Tatsuya Morofuji et al.

Summary: This study reveals the crucial role of acid in the dearomative photocycloaddition of quinolines to olefins, enhancing the reactivity of quinolines' triplet state towards olefins.

ORGANIC LETTERS (2021)

添加到收藏夹

Review Chemistry, Organic

Visible-Light-Induced Dearomatizations

Mikiko Okumura et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Cationic silicon Lewis acids in catalysis

Johannes C. L. Walker et al.

NATURE REVIEWS CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Min Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N-Heterocyclic Carbene Boranes

Wen Dai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of Arene Oxides and Oxepines

Zohaib Siddiqi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Organocatalyzed Birch Reduction Driven by Visible Light

Justin P. Cole et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Medicinal

Opportunities for Tapping into Three-Dimensional Chemical Space through a Quaternary Carbon

Tanaji T. Talele

JOURNAL OF MEDICINAL CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Emerging Strategies for C-H Silylation

Sven C. Richter et al.

TRENDS IN CHEMISTRY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Byron K. Peters et al.

SCIENCE (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

Anamitra Chatterjee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Dearomative syn-1,4-Oxyamination

Conghui Tang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Dearomatization of Pyridines via an Energy-Transfer-Catalyzed Intramolecular [4+2] Cycloaddition

Jiajia Ma et al.

CHEM (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process

Zackaria Nairoukh et al.

NATURE CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Physical

Catalytic hydrogen atom transfer from hydrosilanes to vinylarenes for hydrosilylation and polymerization

Parham Asgari et al.

NATURE CATALYSIS (2019)

添加到收藏夹

Article Chemistry, Medicinal

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

Remya Ramesh et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile

Michael W. Gribble et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic enantioselective Minisci-type addition to heteroarenes

Rupert S. J. Proctor et al.

SCIENCE (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Earth-abundant transition metal catalysts for alkene hydrosilylation and hydroboration

Jennifer V. Obligacion et al.

NATURE REVIEWS CHEMISTRY (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in chemical dearomatization of nonactivated arenes

William C. Wertjes et al.

CHEMICAL SOCIETY REVIEWS (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates

Michael C. Hilton et al.

SCIENCE (2018)

添加到收藏夹

Article Chemistry, Medicinal

Design and expeditious synthesis of organosilanes as potent antivirals targeting multidrug-resistant influenza A viruses

Yanmei Hu et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Electron-Transfer and Hydride-Transfer Pathways in the Stoltz-Grubbs Reducing System (KOtBu/Et3SiH)

Andrew J. Smith et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

C-H Functionalization of Azines

Kei Murakami et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic Dearomatization of N-Heteroarenes with Silicon and Boron Compounds

Sehoon Park et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Dearomative dihydroxylation with arenophiles

Emma H. Southgate et al.

NATURE CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-catalyzed enantioselective arylation of pyridine

J. Patrick Lutz et al.

CHEMICAL SCIENCE (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C-Si Bonds

Narasimhulu Gandhamsetty et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Multidisciplinary Sciences

Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst

Anton A. Toutov et al.

NATURE (2015)

添加到收藏夹

Article Chemistry, Medicinal

Rings in Drugs

Richard D. Taylor et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp3 C-Si Bond Formation

Narasimhulu Gandhamsetty et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Review Chemistry, Organic

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Marcus Baumann et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Medicinal

Organosilicon Molecules with Medicinal Applications

Annaliese K. Franz et al.

JOURNAL OF MEDICINAL CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Organic

Heterocycles in drugs and drug discovery

A. Gomtsyan

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Dearomatization Strategies in the Synthesis of Complex Natural Products

Stephane P. Roche et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

添加到收藏夹

Article Chemistry, Medicinal

Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

Frank Lovering et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

添加到收藏夹

Article Chemistry, Medicinal

A novel class of cycloalkano[b]pyridines as potent and orally active opioid receptor-like 1 antagonists with minimal binding affinity to the hERG K+ channel

Takashi Yoshizumi et al.

JOURNAL OF MEDICINAL CHEMISTRY (2008)

添加到收藏夹

Article Chemistry, Organic

Hydroxide ion as electron source for photochemical Birch-type reduction and photodehalogenation

Yasuharu Yoshimi et al.

TETRAHEDRON LETTERS (2008)

添加到收藏夹

Review Chemistry, Organic

Allylsilanes in organic synthesis - Recent developments

L Chabaud et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2004)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones

SE Denmark et al.

CHEMICAL REVIEWS (2003)

添加到收藏夹

Review Pharmacology & Pharmacy

Chemistry challenges in lead optimization: silicon isosteres in drug discovery

GA Showell et al.

DRUG DISCOVERY TODAY (2003)

添加到收藏夹

Review Chemistry, Multidisciplinary

Transition-metal-mediated dearomatization reactions

AR Pape et al.

CHEMICAL REVIEWS (2000)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.