Strain-Promoted Azide-Alkyne Cycloadditions of Benzocyclononynes

被引：44

作者：

Tummatorn, Jumreang ^{[1
]}

Batsomboon, Paratchata ^{[1
]}

Clark, Ronald J. ^{[1
]}

Alabugin, Igor V. ^{[1
]}

Dudley, Gregory B. ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 05期

基金：

美国国家科学基金会;

关键词：

CLICK CHEMISTRY; STABILIZATION;

D O I：

10.1021/jo300188y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preliminary studies related to the design and development of new cycloalkyne reagents for metal-free click coupling are reported. Cydononynes are more stable than cyclooctynes, and the robust benzocyclononyne platform offers spontaneous reactivity toward azides at rates competitive with other azidophiles that have been employed for metal-free click coupling. Benzocyclononynes (e.g., 1) provide valuable insight into the design of new cycloalkynes for strain-promoted azide-alkyne cydoaddition (SPAAC) couplings for applications in which side reactions and decomposition of the reagent must be kept to a minimum.

引用

页码：2093 / 2097

页数：5

共 50 条

[1] Strain-Promoted Azide-Alkyne Cycloaddition
Liao, Yiming
Wu, Baoqi
Tang, Rongzhi
Lin, Feng
Tan, Yu
[J]. PROGRESS IN CHEMISTRY, 2022, 34 (10) : 2134 - 2145
[2] Plasma induced acceleration and selectivity in strain-promoted azide-alkyne cycloadditions
Warther, David
Dursun, Enes
Recher, Marion
Ursuegui, Sylvain
Mosser, Michel
Sobska, Joanna
Krezel, Wojciech
Chaubet, Guilhem
Wagner, Alain
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (23) : 5063 - 5067
[3] Investigation of Strain-Promoted Azide-Alkyne Cycloadditions in Aqueous Solutions by Capillary Electrophoresis
Steflova, Jana
Storch, Golo
Wiesner, Sarah
Stockinger, Skrollan
Berg, Regina
Trapp, Oliver
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 604 - 613
[4] A Survey of Strain-Promoted Azide-Alkyne Cycloaddition in Polymer Chemistry
Li, Kelvin
Fong, Darryl
Meichsner, Eric
Adronov, Alex
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (16) : 5057 - 5073
[5] Mechanical Reversibility of Strain-Promoted Azide-Alkyne Cycloaddition Reactions
Jacobs, Monique J.
Schneider, Guenter
Blank, Kerstin G.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) : 2899 - 2902
[6] Chemoselectivity of Tertiary Azides in Strain-Promoted Alkyne-Azide Cycloadditions
Svatunek, Dennis
Houszka, Nicole
Hamlin, Trevor A.
Bickelhaupt, F. Matthias
Mikula, Hannes
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (03) : 754 - 758
[7] Strain-Promoted Azide-Alkyne Cycloaddition with Ruthenium(II)-Azido Complexes
Cruchter, Thomas
Harms, Klaus
Meggers, Eric
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) : 16682 - 16689
[8] One Scaffold, Many Possibilities - Copper(I)-Catalyzed Azide-Alkyne Cycloadditions, Strain-Promoted Azide-Alkyne Cycloadditions, and Maleimide-Thiol Coupling of Ruthenium(II) Polypyridyl Complexes
Stumper, Anne
Laemmle, Martin
Mengele, Alexander K.
Sorsche, Dieter
Rau, Sven
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (05) : 586 - 596
[9] Orthogonal, metal-free surface modification by strain-promoted azide-alkyne and nitrile oxide-alkene/alkyne cycloadditions
Wendeln, Christian
Singh, Ishwar
Rinnen, Stefan
Schulz, Christian
Arlinghaus, Heinrich F.
Burley, Glenn A.
Ravoo, Bart Jan
[J]. CHEMICAL SCIENCE, 2012, 3 (08) : 2479 - 2484
[10] Accelerating Strain-Promoted Azide-Alkyne Cycloaddition Using Micellar Catalysis
Anderton, Grant I.
Bangerter, Alyssa S.
Davis, Tyson C.
Feng, Zhiyuan
Furtak, Aric J.
Larsen, Jared O.
Scroggin, Triniti L.
Heemstra, Jennifer M.
[J]. BIOCONJUGATE CHEMISTRY, 2015, 26 (08) : 1687 - 1691

← 1 2 3 4 5 →