Work

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

Year: 2017

Type: article

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.

Source: Angewandte Chemie

DOI: 10.1002/ange.201612288

Authors: Ciaran P. Seath, Glenn A. Burley, Allan J. B. Watson

Institution: University of Strathclyde

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Alexander von Humboldt-Stiftung, Swansea University, Engineering and Physical Sciences Research Council

OpenAlex ID: W4243521095

FWCI: 1.106

Cites: 29

Cited by: 12

Related to: 10