Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Determining the Origin of Rate-Independent Chemoselectivity in CuAAC Reactions: An Alkyne-Specific Shift in Rate-Determining Step.

Literature DB >> 28206700

Determining the Origin of Rate-Independent Chemoselectivity in CuAAC Reactions: An Alkyne-Specific Shift in Rate-Determining Step.

Ciaran P Seath¹, Glenn A Burley¹, Allan J B Watson¹.

Abstract

We report a kinetic and spectroscopic analysis of alkyne-dependent chemoselectivity in the copper-catalyzed azide-alkyne click (CuAAC) reaction. Studies of six alkyne subtypes reveal that the rate-determining step (RDS) of an aromatic ynamine class is shifted from acetylide formation to the azide ligation/migratory insertion event allowing chemoselectivity independent of overall rate.

Entities: Chemical

Keywords: CuAAC; chemoselectivity; click reactions; reaction kinetics; ynamine

Year: 2017 PMID： 28206700 DOI： 10.1002/anie.201612288

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

7 in total

1. Cu(I)-Catalyzed Alkynylation of Quinolones.

Authors: Aitor Maestro; Sebastien Lemaire; Syuzanna R Harutyunyan
Journal: Org Lett Date: 2022-01-31 Impact factor: 6.005

2. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) by Functionalized NHC-Based Polynuclear Catalysts: Scope and Mechanistic Insights.

Authors: Miguel González-Lainez; Miguel Gallegos; Julen Munarriz; Ramón Azpiroz; Vincenzo Passarelli; M Victoria Jiménez; Jesús J Pérez-Torrente
Journal: Organometallics Date: 2022-07-15 Impact factor: 3.837

3. Electrochemical Studies of the Cycloaddition Activity of Bismuth(III) Acetylides Towards Organic Azides Under Copper(I)-Catalyzed Conditions.

Authors: Antonina L Nazarova; Billal Zayat; Valery V Fokin; Sri R Narayan
Journal: Front Chem Date: 2022-02-25 Impact factor: 5.545

Determining the Origin of Rate-Independent Chemoselectivity in CuAAC Reactions: An Alkyne-Specific Shift in Rate-Determining Step.

1. Cu(I)-Catalyzed Alkynylation of Quinolones.

2. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) by Functionalized NHC-Based Polynuclear Catalysts: Scope and Mechanistic Insights.

3. Electrochemical Studies of the Cycloaddition Activity of Bismuth(III) Acetylides Towards Organic Azides Under Copper(I)-Catalyzed Conditions.

4. Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes.

5. A flow platform for degradation-free CuAAC bioconjugation.

6. Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.

Review 7. Preparation and Utility of N-Alkynyl Azoles in Synthesis.