Open AccessCu(I)-azidopyrrolo[3,2-d]pyrimidine Catalyzed Glaser–Hay Reaction under Mild Conditions
Author(s) -
Arun Kumar Thangarasu,
Velickakathu O. Yadhukrishnan,
K. A. Krishnakumar,
Sanjay Suresh Varma,
Ravi S. Lankalapalli
Publication year - 2021
Publication title -
acs organic and inorganic au
Language(s) - English
Resource type - Journals
ISSN - 2694-247X
DOI - 10.1021/acsorginorgau.1c00015
Subject(s) - pyrimidine , substrate (aquarium) , tetrazole , catalysis , chemistry , hay , combinatorial chemistry , medicinal chemistry , reaction conditions , stereochemistry , organic chemistry , agronomy , biology , oceanography , geology
The limitation of the CuAAC "click" reaction with a 2-azidopyridine substrate, owing to its equilibrium with a tetrazole isomer, is exploited herein for its utility in the Glaser-Hay reaction. A catalytic combination of a 2-azidopyridine analogue, 4-azido-5 H -pyrrolo[3,2- d ]pyrimidine, and CuI afforded homocoupled products of terminal alkynes, without any trace of triazole product, under mild conditions with a broad substrate scope. Emphasis on carbohydrate-based substrates appended to a propargylic group led to 1,3-diynes in good to excellent yields.