Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 37, Pages 9503-9507Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100795
Keywords
azaborinines; nitrogen heterocycles; cyclization; metallacycles; structure elucidation
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Funding
- Fonds der Chemischen Industrie (FCI)
- 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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