Rhodium-catalyzed insertion of nitrenes into B–H bonds

30 April 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The paper presents a new method for the formation of B-N bond by the catalytic insertion of nitrenes into organic boranes. The reaction proceeds most selectively for cyclic boranes with 2-phenylpyridine framework and nitrenes generated in situ by oxidation sulfonamides and sulfamates. The most effective catalysts for the process are rhodium and ruthenium carboxylates of [M2(OOCR)4]X type. Complexes with NTTL ligands derived from S-tert-leucine provide chiral products with stereogenic boron atoms. The developed approach can be useful for the introduction of boron heterocycles into functional materials and biologically active molecules.

Keywords

borane
nitrene
insertion
asymmetric catalysis
rhodium carboxylates
B-N bond
stereogenic boron

Supplementary materials

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Description
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Supporting information
Description
Experimental procedures, mechanistic experiments, NMR spectra, HPLC traces, details of crystallographic experiments
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X-ray structures
Description
Combined CIF file with X-ray structures for the compounds 2a, 2f, 2ab, 2jd, and 3a
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