**4. Conclusions**

In conclusion, methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1*H*-pyrrole-2-carboxylate **1** was synthesized on 10-gram scale using iridium-catalyzed C–H borylation. The borylated pyrrole was successfully employed in Suzuki coupling reactions to prepare a variety of 5-(hetero)aryl substituted pyrrole-2-carboxylates. This catalytic borylation–Suzuki coupling synthetic route has several advantages over direct arylation protocols including compatibility with NH2, OH, and pyrrole N-H functional groups, retention of chloro substituents for further functionalization, installation of highly electron-rich aromatic rings, and preparation of bi-heteroaryls including α-β linked bi-pyrrole.

**Supplementary Materials:** The following are available online at http://www.mdpi.com/1420-3049/25/9/2106/s1, 1H and 13C NMR spectra of the synthesized compounds.

**Author Contributions:** Conceptualization, G.A.C.; methodology, G.A.C., and S.K.; validation, S.K., S.F., and M.I.; formal analysis, G.A.C.; investigation, S.K., N.-u.-A., S.F., A.-H.E., and M.A.; resources, X.G., and G.A.C.; data curation, A.-H.E., and G.A.C.; writing—original draft preparation, G.A.C., and S.K.; writing—review and editing, R.S.Z.S., S.F., M.I., and G.A.C.; visualization, G.A.C.; supervision, G.A.C.; project administration, G.A.C.; funding acquisition, M.A. and G.A.C. All authors have read and agreed to the published version of the manuscript.

**Funding:** This research was funded by HIGHER EDUCATION COMMISION OF PAKISTAN, grant number NRPU-4426, and by LAHORE UNIVERSITY OF MANAGEMENT SCIENCES through start-up and faculty initiative fund to G.A.C.

**Acknowledgments:** We extend our acknowledgement to KAUST core labs facilities for NMR and HRMS measurements.

**Conflicts of Interest:** The authors declare no conflict of interest.
