Cu(I)-azidopyrrolo[3,2- d]pyrimidine Catalyzed Glaser-Hay Reaction under Mild Conditions

Arun K Thangarasu; Velickakathu O Yadhukrishnan; K A Krishnakumar; Sanjay Suresh Varma; Ravi S Lankalapalli

doi:10.1021/acsorginorgau.1c00015

Cu(I)-azidopyrrolo[3,2- d]pyrimidine Catalyzed Glaser-Hay Reaction under Mild Conditions

ACS Org Inorg Au. 2021 Aug 20;2(1):3-7. doi: 10.1021/acsorginorgau.1c00015. eCollection 2022 Feb 2.

Authors

Arun K Thangarasu^{1

2}, Velickakathu O Yadhukrishnan¹, K A Krishnakumar^{1

2}, Sanjay Suresh Varma¹, Ravi S Lankalapalli^{1

2}

Affiliations

¹ Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, India.
² Academy of Scientific & Innovative Research (AcSIR), Ghaziabad-201002, India.

Abstract

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-5H-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.