Desymmetrization of Diboron(4) by a Trifluorination B-Masking Strategy: Practical Synthesis of Unsymmetrical Diboron Species.

J Org Chem

Institute of Chemistry, The Center for Nanoscience and Nanotechnology, and Casali Center for Applied Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel.

Published: August 2024

Herein, we report a straightforward practical and simple method for efficiently synthesizing a BF-containing unsymmetrical diboron salt. This method involves the direct desymmetrization of commercially available diboron(4). This desymmetrization is based on a selective B-masking strategy via nucleophilic trifluorination, providing the elusive diborons bearing a trifluoroborate group. The synthetic utility of these salts is demonstrated through various examples of (sequential) B-ligand interconversions, enabling the synthesis of unsymmetrical diboron derivatives. These products, which serve as valuable building blocks, are obtained in gram-scale and high yields.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11334178PMC
http://dx.doi.org/10.1021/acs.joc.4c00715DOI Listing

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