Issue 47, 2021

Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums

Abstract

Metal-catalyzed mono-acylmethylation of pyridylcarboranes has been realized using α-carbonyl sulfoxonium ylides as a coupling partner. The reaction features high efficiency, excellent site-selectivity and good functional group tolerance. In the presence of pyridyl and enolizable acylmethyl groups, a post-coordination mode has been proposed and validated by in situ high resolution mass spectroscopy (HRMS) to rationalize the unique mono-substitution. Post-functionalization at the newly incorporated alkyl site provides additional utility of this method, including the construction of carborane-fused indoliziniums and quinoliziniums. We believe that these mono-alkylated carboranes, together with their post-functionalized derivatives, may find applications in luminescent materials and drug discovery in the near future.

Graphical abstract: Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Sep 2021
Accepted
19 Nov 2021
First published
19 Nov 2021
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., 2021,12, 15563-15571

Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums

H. Cao, X. Wei, F. Sun, X. Zhang, C. Lu and H. Yan, Chem. Sci., 2021, 12, 15563 DOI: 10.1039/D1SC05296A

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