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Lithium Dihydropyridine Dehydrogenation Catalysis: A Group 1 Approach to the Cyclization of Diamine Boranes
Author(s) -
McLellan Ross,
Kennedy Alan R.,
Orr Samantha A.,
Robertson Stuart D.,
Mulvey Robert E.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610905
Subject(s) - boranes , dehydrogenation , chemistry , catalysis , diamine , alkyl , ruthenium , lithium (medication) , organic chemistry , combinatorial chemistry , medicinal chemistry , boron , medicine , endocrinology
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.