Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

Jun Kikuchi; Roi Nakajima; Naohiko Yoshikai

doi:10.3762/bjoc.20.79

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

Beilstein J Org Chem. 2024 Apr 22:20:891-897. doi: 10.3762/bjoc.20.79. eCollection 2024.

Authors

Jun Kikuchi¹, Roi Nakajima¹, Naohiko Yoshikai¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

Abstract

A stereoselective N-alkenylation of azoles with alkynes and iodine(III) electrophile is reported. The reaction between various azoles and internal alkynes is mediated by benziodoxole triflate as the electrophile in a trans-fashion, affording azole-bearing vinylbenziodoxoles in moderate to good yields. The tolerable azole nuclei include pyrazole, indazole, 1,2,3-triazole, benzotriazole, and tetrazole. The iodanyl group in the product can be leveraged as a versatile synthetic handle, allowing for the preparation of hitherto inaccessible types of densely functionalized N-vinylazoles.

Keywords: alkynes; azoles; cross-coupling; hypervalent iodine.

Grants and funding

This work was supported by JSPS KAKENHI (Grant No. 20K23375 (N.Y.) and 19K15552 (J.K.)), The Uehara Memorial Foundation (N.Y.), Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED (Grant No. JP23ama121040 (N.Y.)).