Issue 27, 2024

A Pd-catalyzed route to carborane-fused boron heterocycles

Abstract

Due to the expanding applications of icosahedral carboranes in medicinal and materials chemistry research, their functionalizations have become one of the central themes in boron-rich cluster chemistry. Although several strategies for incorporating nitrogen-containing nucleophiles on a single boron vertex of the icosahedral carboranes (C2B10H12) have been developed, methods for preparing clusters with vicinal B–N moieties are still lacking. The steric bulk of icosahedral carboranes and disparate electronic and steric nature of the N-containing groups have rendered the vicinal diamination challenging. In this article, we show how a developed Pd-catalyzed process is used to incorporate an array of NH-heterocycles, anilines, and heteroanilines with various electronic and steric profiles onto the vicinal boron vertices of a meta-carborane cluster via sequential or one-pot fashion. Importantly, oxidative cyclizations of the cross-coupling products with indoles and pyrroles appended to boron vertices generate a previously unknown class of all-boron-vertex bound carborane-fused six- and seven-membered ring heterocycles. Photophysical studies of the meta-carborane-fused heterocycles show that these structures can exhibit luminescence with high quantum yields and are amenable to further manipulations.

Graphical abstract: A Pd-catalyzed route to carborane-fused boron heterocycles

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Apr 2024
Accepted
28 May 2024
First published
28 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 10392-10401

A Pd-catalyzed route to carborane-fused boron heterocycles

M. Zhu, P. Wang, Z. Wu, Y. Zhong, L. Su, Y. Xin, A. M. Spokoyny, C. Zou and X. Mu, Chem. Sci., 2024, 15, 10392 DOI: 10.1039/D4SC02214A

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