Tosylazide as N1-Synthon: Iron-Catalyzed Nitrogenative Dimerization of Indoles to p-Bisindolopyrazine Derivatives

Jianan Li; Xiaohan Sun; Evgenia Dmitrieva; Noel Israel; Fupeng Wu; Lin Yang; Renxiang Liu; Xinliang Feng; Bernd Plietker

doi:10.1021/acs.orglett.3c04209

Tosylazide as N1-Synthon: Iron-Catalyzed Nitrogenative Dimerization of Indoles to p-Bisindolopyrazine Derivatives

Org Lett. 2024 Feb 9;26(5):1046-1050. doi: 10.1021/acs.orglett.3c04209. Epub 2024 Jan 31.

Authors

Jianan Li¹, Xiaohan Sun¹, Evgenia Dmitrieva², Noel Israel², Fupeng Wu^{3

4}, Lin Yang³, Renxiang Liu³, Xinliang Feng^{3

4}, Bernd Plietker¹

Affiliations

¹ Chair of Organic Chemistry I, Faculty of Chemistry and Food Chemistry, TU Dresden, Bergstraße 66, DE-01069 Dresden, Germany.
² Leibniz Institute for Solid State and Materials Research, DE-01069 Dresden, Germany.
³ Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, TU Dresden, Mommsenstrasse 4, DE-01062 Dresden, Germany.
⁴ Max Planck Institute of Microstructure Physics Weinberg 2, 06120 Halle, Germany.

PMID: 38294841
DOI: 10.1021/acs.orglett.3c04209

Abstract

We present a straightforward one-step process to access a range of novel p-diindolepyrazines via an unprecedented [n-Bu₄N][Fe(CO)₃(NO)] (TBA[Fe])-catalyzed intermolecular nitrogenative dimerization of various indole derivatives. Remarkably, tosylazide functions as a N1-synthon forming the central pyrazine unit that joins the two indole subunits. The catalytic transformation shows a good substrate scope, and the obtained products show interesting electronic properties.