4.6 Article

Rhodium-Mediated Stoichiometric Synthesis of Mono-, Bi-, and Bis-1,2-Azaborinines: 1-Rhoda-3,2-azaboroles as Reactive Precursors

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 37, Pages 9503-9507

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100795

Keywords

azaborinines; nitrogen heterocycles; cyclization; metallacycles; structure elucidation

Funding

  1. Fonds der Chemischen Industrie (FCI)
  2. Deutsche Forschungsgemeinschaft (DFG)

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A series of highly substituted 1,2-azaborinines, including a phenylene-bridged bis-1,2-azaborinine, was successfully synthesized in this study. The new method using rhodacycles instead of 1,2-azaborete complexes as precursors proved to be more effective in the synthesis of a wider range of 1,2-azaborinines.
A series of highly substituted 1,2-azaborinines, including a phenylene-bridged bis-1,2-azaborinine, was synthesized from the reaction of 1,2-azaborete rhodium complexes with variously substituted alkynes. 1-Rhoda-3,2-azaborole complexes, which are accessible by phosphine addition to the corresponding 1,2-azaborete complexes, were also found to be suitable precursors for the synthesis of 1,2-azaborinines and readily reacted with alkynyl-substituted 1,2-azaborinines to generate new regioisomers of bi-1,2-azaborinines, which feature directly connected aromatic rings. Their molecular structures, which can be viewed as boron-nitrogen isosteres of biphenyls, show nearly perpendicular 1,2-azaborinine rings. The new method using rhodacycles instead of 1,2-azaborete complexes as precursors is shown to be more effective, allowing the synthesis of a wider range of 1,2-azaborinines.

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