A General Sonogashira-Type Strategy for Exopolyhedral B–C(sp) Bond Formation on o - and m -Carboranes

Organic Letters 2026 Open access

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Authors: Charis A. Hinkle, Aidan T. Tiffany, Alexander P. Luancing, Lars Lefkowitz, Jessica Sampson, Glenn P. A. Yap, Marco S. Messina
DOI: 10.1021/acs.orglett.6c01141
Cited by: 1
References: 57

Abstract

We report our discovery that tricyclohexyl phosphine is a privileged ligand that enables highly efficient Pd-catalyzed B–C(sp) bond formation on iodinated carborane precursors. We display the generality and utility of our reaction framework in the alkynylation of 9-I- m -carborane and demonstrate the first examples of monoalkynylation and symmetric dialkynylation on 9-I- o -carborane and 9,10-I 2 - m -carborane, respectively, under Sonogashira-type cross-coupling conditions across a broad range of diverse and complex alkyne-terminated coupling partners.

Fields of Study & Subjects

Boron Compounds in Chemistry Organoboron and organosilicon chemistry Radiopharmaceutical Chemistry and Applications

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
17
Pages
5515–5520
Publication date
21 April 2026
Language
EN