Nickel-Catalyzed Reductive Coupling of Aryl Halides with 10BF3 to Access Isotopically Labelled Boronates

Martin Oestreich; Hendrik F. T. Klare; Emilio Acuña-Bolomey

doi:10.1055/a-2739-0228

Synfacts, Table of Contents

Synfacts 2026; 22(01): 34
DOI: 10.1055/a-2739-0228

Metals in Synthesis

Nickel-Catalyzed Reductive Coupling of Aryl Halides with ¹⁰BF₃ to Access Isotopically Labelled Boronates

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Abstract

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Meng C-F, Zhang B-B, Liu S, Liu Q, Wang Z-X *, Chen X-Y *. University of the Chinese Academy of Sciences, Beijing and Binzhou Institute of Technology, P. R. China
Direct Boron-10 Access: Nickel-Catalyzed Reductive C(sp²)–¹⁰B Coupling Utilizing ¹⁰BF₃ .

Angew. Chem. Int. Ed. 2025;
64: e202513304
DOI: 10.1002/anie.202513304

Keywords

aryl halides - ¹⁰BF₃ - C(sp²)–¹⁰B coupling - isotopic labelling - nickel catalysis - reductive coupling

Significance

A nickel-catalyzed protocol for the direct reductive C(sp²)–¹⁰B coupling of aryl halides with commercially available ¹⁰BF₃ is reported. Key to success is the in situ generation of an electrophilic borenium ion from ¹⁰BF₃ using AlCl₃ and Hünig's base.

Comment

This novel protocol provides direct access to various isotopically enriched ¹⁰B organoboron compounds that can be used in boron neutron capture therapy (BNCT) and in neutron shielding materials.

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