☆ 4.8 Article

Remote Strain Activation in a Sulfate-Linked Dibenzocycloalkyne

ORGANIC LETTERS (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, Organic

SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride

Pavel Yamanushkin et al.

Summary: This study presents a facile strategy to synthesize SuFExable NH-pyrazoles via strain and catalyst-free 1,3-dipolar cycloadditions of stabilized diazo compounds under mild conditions. Subsequent SuFEx reactions can efficiently proceed with various N- and O-nucleophiles. The access to SuFExable NH-pyrazoles, which contain two common pharmacophores, opens up new opportunities in drug discovery, chemical biology, materials chemistry, and related fields.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Uncovering the Key Role of Distortion in Bioorthogonal Tetrazine Tools That Defy the Reactivity/Stability Trade-Off

Dennis Svatunek et al.

Summary: The tetrazine/trans-cyclooctene ligation, with its exceptional reaction kinetics, has significant potential for various molecular technologies. This study explores the factors that contribute to the high reactivity observed in tetrazines. Contrary to previous beliefs, it is found that intramolecular N-N interaction, rather than electron-withdrawing effects, plays a key role in accelerating the reaction. Additionally, the stability of tetrazines is influenced by the electron-withdrawing effects, while intramolecular repulsion increases reactivity without compromising stability. These findings provide valuable insights into the reactivity/stability trade-off for tetrazines in physiologically relevant environments and may facilitate the rational design of bioorthogonal tools.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design

Steven E. Beutick et al.

Summary: The 1,3-dipolar cycloaddition reaction has proven immensely useful in organic, material, and biological chemistry, with metal catalysis and predistortion or electronic tuning of the dipolarophile enhancing reactivity. Quantum chemical calculations are critical for understanding physical factors controlling reactivity and selectivity, and design principles derived from in silico calculations are invaluable for tailored reactivity of new dipolarophiles.

CHEMISTRY-AN ASIAN JOURNAL (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Mechanisms and Substituent Effects of Metal-Free Bioorthogonal Reactions

Titas Deb et al.

Summary: This article reviews the mechanisms and substituent effects of some of the principal metal-free bioorthogonal reactions, based on inverse-electron demand Diels-Alder reactions, 1,3-dipolar cycloadditions, and the Staudinger reaction. Modified versions that link these reactions to a dissociative step are further discussed, with the aim to aid the advancement of bioorthogonal chemistry.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Heterocycloalkynes Fused to a Heterocyclic Core: Searching for an Island with Optimal Stability-Reactivity Balance

Natalia A. Danilkina et al.

Summary: Novel cycloalkynes were created by integrating reagent destabilization and transition state stabilization approaches, leading to stable and active SPAAC reagents for bioorthogonal bioconjugation. Computational and experimental studies showed similar SPAAC reactivities for different heterocyclic cycloalkynes. The stability-reactivity balance of strained systems is influenced by the interplay of two electronic effects.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning

Jesus M. Dones et al.

Summary: The study integrated two strategies to optimize alkynyl reagents for achieving high reaction rates. Computational analysis indicated that aryl substitution could be beneficial for increasing reactivity. Experimental results showed that interactions between the new reagents and amino dipolarophile contribute to enhanced reaction efficiency.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone

Igor Alabugin et al.

Summary: Although carbon is crucial in organic chemistry, it is oxygen that plays a central role in stereoelectronic control. Oxygen can adapt to different situations in various transformations and its interactions play a key role in chemical reactivity. Understanding the fundamental connections between the anomeric effect and different oxygen functionalities is essential for predicting reactivity and designing new synthetic transformations.

CHEMICAL SOCIETY REVIEWS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition

Martin Breugst et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Developing bioorthogonal probes to span a spectrum of reactivities

Sean S. Nguyen et al.

NATURE REVIEWS CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes

Yun Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of NMs-DACN: Small and Hydrophilic Click Reaction Device

Yuuya Kawasaki et al.

CHEMISTRY LETTERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Strain and stereoelectronics in cycloalkyne click chemistry

Trevor Harris et al.

MENDELEEV COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chemoselectivity of Tertiary Azides in Strain-Promoted Alkyne-Azide Cycloadditions

Dennis Svatunek et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

添加到收藏夹

Article Chemistry, Organic

Reactivity of the Sultam and Strained Alkyne Groups in 2-Aminobenzenesulfonamide-Containing Cyclononyne (ABSACN)

Kyosuke Kaneda et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups

Sergey Z. Vatsadze et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs

Eileen G. Burke et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Organic

2-Aminobenzenesulfonamide-Containing Cyclononyne as Adjustable Click Reagent for Strain-Promoted Azide-Alkyne Cycloaddition

Kyosuke Kaneda et al.

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Organic

Thieme Chemistry Journals Awardees: Where Are They Now? One-Pot Synthesis of Versatile Buckle Units for Click Chemistry: 4,8-Diazacyclononynes (DACNs)

Kazunobu Igawa et al.

SYNLETT (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Twisted Cycloalkynes and Remote Activation of Click'' Reactivity

Trevor Harris et al.

CHEM (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model

F. Matthias Bickelhaupt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Review Biochemistry & Molecular Biology

Diazo Compounds: Versatile Tools for Chemical Biology

Kalie A. Mix et al.

ACS CHEMICAL BIOLOGY (2016)

添加到收藏夹

Article Chemistry, Organic

Decreasing Distortion Energies without Strain: Diazo-Selective 1,3-Dipolar Cycloadditions

Brian Gold et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Organic

1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain

Brian Gold et al.

ORGANIC LETTERS (2016)

添加到收藏夹

Article Chemistry, Organic

1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides

Matthew R. Aronoff et al.

ORGANIC LETTERS (2016)

添加到收藏夹

Article Chemistry, Organic

Rapid cycloaddition of a diazo group with an unstrained dipolarophile

Matthew R. Aronoff et al.

TETRAHEDRON LETTERS (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

Jan Dommerholt et al.

TOPICS IN CURRENT CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diazo Groups Endure Metabolism and Enable Chemoselectivity in Cellulo

Kristen A. Andersen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Heteroatom-embedded Medium-Sized Cycloalkynes: Concise Synthesis, Structural Analysis, and Reactions

Runyan Ni et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Review Biochemistry & Molecular Biology

Finding the Right (Bioorthogonal) Chemistry

David M. Patterson et al.

ACS CHEMICAL BIOLOGY (2014)

添加到收藏夹

Article Chemistry, Organic

Alkynyl Crown Ethers as a Scaffold for Hyperconjugative Assistance in Noncatalyzed Azide-Alkyne Click Reactions: Ion Sensing through Enhanced Transition-State Stabilization

Brian Gold et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Organic

A Homologation Approach to the Synthesis of Difluorinated Cycloalkynes

Ellen M. Sletten et al.

ORGANIC LETTERS (2014)

添加到收藏夹

Article Biochemistry & Molecular Biology

Optimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications

Eun J. Kim et al.

CARBOHYDRATE RESEARCH (2013)

添加到收藏夹

Article Chemistry, Organic

Electronic Effects versus Distortion Energies During Strain-Promoted Alkyne-Azide Cycloadditions: A Theoretical Tool to Predict Reaction Kinetics

Jaime Garcia-Hartjes et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

1-Thiacyclooct-4-yne (=5,6-Didehydro-3,4,7,8-tetrahydro-2H-thiocin), and Its Sulfoxide and Its Sulfone

Hans Schuhmacher et al.

HELVETICA CHIMICA ACTA (2013)

添加到收藏夹

Article Chemistry, Organic

Two Functional Groups in One Package: Using Both Alkyne π-Bonds in Cascade Transformations

Igor V. Alabugin et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Moderating Strain without Sacrificing Reactivity: Design of Fast and Tunable Noncatalyzed Alkyne-Azide Cycloadditions via Stereoelectronically Controlled Transition State Stabilization

Brian Gold et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Thiacycloalkynes for Copper-Free Click Chemistry

Gabriela de Almeida et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Article Chemistry, Organic

Selective Transition State Stabilization via Hyperconjugative and Conjugative Assistance: Stereoelectronic Concept for Copper-Free Click Chemistry

Brian Gold et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

添加到收藏夹

Article Chemistry, Organic

Strain-Promoted Azide-Alkyne Cycloadditions of Benzocyclononynes

Jumreang Tummatorn et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry

Chelsea G. Gordon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Article Chemistry, Organic

Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations

Christopher D. McNitt et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes

Nicholas A. McGrath et al.

CHEMICAL SCIENCE (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells

Jan Dommerholt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

添加到收藏夹

Article Biochemical Research Methods

Surface Functionalization Using Catalyst-Free Azide-Alkyne Cycloaddition

Alexander Kuzmin et al.

BIOCONJUGATE CHEMISTRY (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition

Marjoke F. Debets et al.

CHEMICAL COMMUNICATIONS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones

John C. Jewett et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

添加到收藏夹

Review Chemistry, Multidisciplinary

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

Ellen M. Sletten et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ring Strain Energy in the Cyclooctyl System. The Effect of Strain Energy on [3+2] Cycloaddition Reactions with Azides

Robert D. Bach

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reactivity and Regioselectivity in 1,3-Dipolar Cycloadditions of Azides to Strained Alkynes and Alkenes: A Computational Study

Franziska Schoenebeck et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Selective Labeling of Living Cells by a Photo-Triggered Click Reaction

Andrei A. Poloukhtine et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Article Chemistry, Organic

Cyclooctyne-based reagents for uncatalyzed click chemistry: A computational survey

Kimberly Chenoweth et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions

Xinghai Ning et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

添加到收藏夹

Review Chemistry, Multidisciplinary

Theory of 1,3-dipolar cycloadditions: Distortion/interaction and frontier molecular orbital models

Daniel H. Ess et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

Article Chemistry, Physical

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals

Yan Zhao et al.

THEORETICAL CHEMISTRY ACCOUNTS (2008)

添加到收藏夹

Article Multidisciplinary Sciences

Copper-free click chemistry for dynamic in vivo imaging

Jeremy M. Baskin et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Distortion/Interaction energy control of 1,3-dipolar cycloaddition reactivity

Daniel H. Ess et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems

NJ Agard et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

添加到收藏夹

Article Chemistry, Organic

High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide

BL Nilsson et al.

ORGANIC LETTERS (2001)

添加到收藏夹

Article Chemistry, Organic

A traceless Staudinger ligation for the chemoselective synthesis of amide bonds

E Saxon et al.

ORGANIC LETTERS (2000)

添加到收藏夹

Article Multidisciplinary Sciences

Cell surface engineering by a modified Staudinger reaction

E Saxon et al.

SCIENCE (2000)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.