☆ 4.6 Review

Synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes by cross-coupling induced by transition metals - formation of C-C bonds

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

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

Rapid Access to 2-Substituted Bicyclo[1.1.1]pentanes

Olivia L. Garry et al.

Summary: Replacing aryl rings with saturated carbocyclic structures is of great interest in drug discovery for improved pharmacokinetic properties. However, the synthesis of 2-substituted BCPs remains challenging and nonmodular. This study presents a generalizable strategy for bridge functionalization and demonstrates a streamlined pathway to diverse 2-substituted BCPs through radical C-H abstraction and metallaphotoredox protocols.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Review Agriculture, Multidisciplinary

Applications of Bioisosteres in the Design of Biologically Active Compounds

Nicholas A. Meanwell

Summary: The design of bioisosteres is a creative and productive approach to improve molecules by enhancing potency, addressing pharmacokinetic challenges, reducing off-target liabilities, and modulating physicochemical properties. It is a principle exploited in the design of bioactive compounds in medicinal and agricultural chemistry. This review provides a synopsis of applications where molecular editing through bioisosterism has proven advantageous in molecule optimization, focusing on various examples including carboxylic acids, fluorine and fluorinated motifs, sulfoximine functionality, drug-H2O complexes, and the phenyl ring.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

A General and Modular Approach to BCP Alkylamines via Multicomponent Difunctionalization of [1.1.1]Propellane

Weichen Huang et al.

Summary: Over the past decade, the bicycle[1.1.1]pentane (BCP) motifs have been proven to be valuable bioisosteres of para-disubstituted benzenes in pharmaceuticals. However, the limited approaches and complex syntheses of BCP building blocks are hindering early discovery research in medicinal chemistry. In this study, a modular strategy for preparing functionalized BCP alkylamines was developed, which includes a general method for introducing fluoroalkyl groups to BCP scaffolds using readily available fluoroalkyl sulfinate salts. Furthermore, this strategy can also be extended to incorporate sulfones and thioethers into the BCP core using S-centered radicals. Overall, this multicomponent strategy allows for rapid construction of BCP-type bioisosteres for drug discovery applications.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes

Bethany R. Shire et al.

Summary: Bicyclo[1.1.1]pentanes (BCPs) have emerged as attractive bioisosteres for para-substituted benzene rings in drug design. They offer various advantages compared to aromatic parents and can be synthesized using a wide array of methods. This perspective discusses the evolution of BCP synthesis methods, recent breakthroughs in bridge-substituted BCPs synthesis, and post-synthesis functionalization. The review also explores new challenges and directions in the field, including the emergence of other small ring hydrocarbons and heterocycles with unique substituent exit vectors.

JACS AU (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy

Xiaoxiang Xi et al.

Summary: A method for ketone synthesis was developed using a nickel/photoredox dual-catalysis approach, allowing for the formation of sterically congested ketones under mild conditions. The study identified a Ni-0/Ni-I/Ni-III pathway for ketone formation through combined experimental and computational studies.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Dicarbofunctionalization of [1.1.1]Propellane Enabled by Nickel/Photoredox Dual Catalysis: One-Step Multicomponent Strategy for the Synthesis of BCP-Aryl Derivatives

Weichen Huang et al.

Summary: Bicyclo[1.1.1]pentane (BCP) motifs have become important in pharmaceutical, agrochemical, and materials chemistry. Most of these structures are obtained through the cleavage of the internal C-C bond in [1.1.1]propellane, using either radicals or metal-based nucleophiles. A multicomponent reaction that allows direct access to complex and diverse disubstituted BCP products is more attractive than current stepwise approaches.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Organic

Radical Multicomponent Alkyl Alkynylation of Propellane via Synergistic Photoredox and Copper Catalysis

Jie Shi et al.

Summary: A novel and efficient reaction for synthesizing alkyl-alkynyl-substituted BCP derivatives by synergistic photoredox and copper catalysis at room temperature is described. This procedure offers mild reaction conditions, a simple protocol, broad functional group tolerance, and high efficiency, making it a valuable strategy for accessing alkynyl-substituted BCPs.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Physical

General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction

Angel Renteria-Gomez et al.

Summary: This study presents a conceptually different approach to access diverse (fluoro)alkyl BCP-aryls through an iron-catalyzed multicomponent radical cross-coupling reaction. Experimental and computational mechanistic studies provide insights into the mechanism and ligand effects on C-C bond formation.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

One step synthesis of unsymmetrical 1,3-disubstituted BCP ketones via nickel/photoredox-catalyzed [1.1.1]propellane multicomponent dicarbofunctionalization

Weichen Huang et al.

Summary: A single-step, multi-component approach to versatile disubstituted bicyclo[1.1.1]pentane (BCP) ketones via nickel/photoredox catalysis is reported. This method solves the challenge of preparing unsymmetrical 1,3-disubstituted BCP ketones and demonstrates the synthetic value of transforming them into various other BCP derivatives.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates

Yangyang Yang et al.

Summary: This study presents a novel approach for the synthesis of multisubstituted BCPs via intramolecular cyclization, enabling the construction of underexplored multisubstituted BCPs from readily accessible cyclobutanones. The method demonstrates broad generality through the synthesis of a variety of other caged bicyclic molecules, highlighting the ability to enable the programmed and divergent synthesis of multisubstituted bicyclic hydrocarbons.

NATURE CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives

Joseph M. Anderson et al.

Summary: By replacing aromatic rings, internal alkynes, and tert-butyl groups with bicyclo[1.1.1]pentane (BCP) units, the saturation level and three-dimensionality of drug-like compounds can be increased to enhance their potency and selectivity. While functionalization of the tertiary bridgehead positions of BCP derivatives is well-studied, functionalization of the three concyclic secondary bridge positions is still a developing field. The unique properties of the BCP core present synthetic challenges but offer novel vectors for drug discovery and applications in materials science.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation

Viktor C. Polites et al.

Summary: This study reports the synthesis and Ni-catalyzed functionalization of BCP redox-active esters with (hetero)aryl bromides via the action of a photoactive electron donor-acceptor complex.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates

Russell A. Shelp et al.

Summary: In this study, a new three-component reaction was reported for the synthesis of benzylamine bicyclo[1.1.1]pentane pinacol boronates, demonstrating the versatility of boronate esters and their successful application to challenging tertiary pinacol boronates.

CHEMICAL SCIENCE (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Silaboration of [1.1.1]Propellane: A Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives

Masaki Kondo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Divergent Strain-Release Amino-Functionalization of [1.1.1]Propellane with Electrophilic Nitrogen-Radicals

Ji Hye Kim et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Copper-mediated synthesis of drug-like bicyclopentanes

Xiaheng Zhang et al.

NATURE (2020)

添加到收藏夹

Article Chemistry, Organic

Continuous Flow-Enabled Synthesis of Bench-Stable Bicyclo[1.1.1]pentane Trifluoroborate Salts and Their Utilization in Metallaphotoredox Cross-Couplings

Michael D. VanHeyst et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling

Jeremy Nugent et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents

Claire Andersen et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-catalysed photoinduced decarboxylative alkynylation: a combined experimental and computational study

Yu Mao et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rationalizing the diverse reactivity of [1.1.1] propellane through σ-π-delocalization

Alistair J. Sterling et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Enantioenriched α-Chiral Bicyclo[1.1.1]pentanes

Marie L. J. Wong et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane

Nisalak Trongsiriwat et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Organic

Aminoalkylation of [1.1.1]Propellane Enables Direct Access to High-Value 3-Alkylbicyclo[1.1.1]pentan-1-amines

Jonathan M. E. Hughes et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Physical

A General Route to Bicyclo[1.1.1]pentanes through Photoredox Catalysis

Jeremy Nugent et al.

ACS CATALYSIS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides

Avijit Hazra et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Multidisciplinary Sciences

A folded viral noncoding RNA blocks host cell exoribonucleases through a conformationally dynamic RNA structure

Anna-Lena Steckelberg et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes

Dimitri F. J. Caputo et al.

CHEMICAL SCIENCE (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Multinuclear iron-phenyl species in reactions of simple iron salts with PhMgBr: identification of Fe4(μ-Ph)6(THF)4 as a key reactive species for cross-coupling catalysis

Stephanie H. Carpenter et al.

CHEMICAL SCIENCE (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of BCP Benzylamines From 2-Azaallyl Anions and [1.1.1]Propellane

Russell A. Shelp et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Alkyl and Aryl Thiol Addition to [1.1.1]Propellane: Scope and Limitations of a Fast Conjugation Reaction

Robin M. Baer et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

添加到收藏夹

Article Chemistry, Medicinal

Investigation of a Bicyclo[1.1.1]pentane as a Phenyl Replacement within an LpPLA(2) Inhibitor

Nicholas D. Measom et al.

ACS MEDICINAL CHEMISTRY LETTERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity

Justin M. Lopchuk et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Radical Multicomponent Carboamination of [1.1.1]Propellane

Junichiro Kanazawa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Medicinal

Toward Resolving the Resveratrol Conundrum: Synthesis and in Vivo Pharmacokinetic Evaluation of BCP-Resveratrol

Yi Ling Goh et al.

ACS MEDICINAL CHEMISTRY LETTERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane

Ilya S. Makarov et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Medicinal

Improving Nonspecific Binding and Solubility: Bicycloalkyl Groups and Cubanes as para-Phenyl Bioisosteres

Yves P. Auberson et al.

CHEMMEDCHEM (2017)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and Biopharmaceutical Evaluation of Imatinib Analogues Featuring Unusual Structural Motifs

Kyriacos C. Nicolaou et al.

CHEMMEDCHEM (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Redox-Active Esters in Fe-Catalyzed C-C Coupling

Fumihiko Toriyama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Multidisciplinary Sciences

Strain-release amination

Ryan Gianatassio et al.

SCIENCE (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions

Robin B. Bedford

ACCOUNTS OF CHEMICAL RESEARCH (2015)

添加到收藏夹

Article Chemistry, Medicinal

Evaluation of tert-Butyl Isosteres: Case Studies of Physicochemical and Pharmacokinetic Properties, Efficacies, and Activities

Matthias V. Westphal et al.

CHEMMEDCHEM (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Activation of Aryl and Heteroaryl Halides by an Iron(I) Complex Generated in the Reduction of [Fe(acac)3] by PhMgBr: Electron Transfer versus Oxidative Addition

Guillaume Lefevre et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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, Applied

Photo-Induced Sonogashira C-C Coupling Reaction Catalyzed by Simple Copper(I) Chloride Salt at Room Temperature

Arunachalam Sagadevan et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

添加到收藏夹

Article Chemistry, Medicinal

Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Ring Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor

Antonia F. Stepan et al.

JOURNAL OF MEDICINAL CHEMISTRY (2012)

添加到收藏夹

Article Multidisciplinary Sciences

Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway

Sidney E. Creutz et al.

SCIENCE (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives

Nicholas A. McGrath et al.

JOURNAL OF CHEMICAL EDUCATION (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

1,3-bicyclo[1.1.1]pentanediyl: The shortest rigid linear connector of phenylated photochromic units and a 1,5-dimethoxy-9,10-di(phenylethynyl)anthracene fluorophore

Armin de Meijere et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Harder than diamond: determining the cross-sectional area and young's modulus of molecular rods

L Itzhaki et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

添加到收藏夹

Article Chemistry, Organic

Synthesis and structure of trigonal and tetragonal connectors for a tinkertoy construction set

PFH Schwab et al.

JOURNAL OF ORGANIC CHEMISTRY (2002)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.