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Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes

In reactions restricted previously to a ruthenium catalyst, a 1‐lithium‐2‐alkyl‐1,2‐dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes into cyclic 1,3,2‐diazaborolidines, which can in turn be smoothly arylated in good y...

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Detalles Bibliográficos
Autores principales: McLellan, Ross, Kennedy, Alan R., Orr, Samantha A., Robertson, Stuart D., Mulvey, Robert E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5396369/
https://www.ncbi.nlm.nih.gov/pubmed/28000994
http://dx.doi.org/10.1002/anie.201610905
Descripción
Sumario:In reactions restricted previously to a ruthenium catalyst, a 1‐lithium‐2‐alkyl‐1,2‐dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes into cyclic 1,3,2‐diazaborolidines, which can in turn be smoothly arylated in good yields. This study established the conditions and solvent dependence of the catalysis through NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X‐ray crystallographic studies of several model lithio intermediates.