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- Title
Azaborabutadienes: Synthesis by Metal-Free Carboboration of Nitriles and Utility as Building Blocks for B,N-Heterocycles.
- Authors
Kong, Lingbing; Lu, Wei; Li, Yongxin; Ganguly, Rakesh; Kinjo, Rei
- Abstract
Metal-free regioselective carboboration of arylnitriles with L2PhB: ( 1: L=oxazol-2-ylidene) catalyzed by Et3B afforded the unprecedented acyclic 2-aza-4-borabutadienes 2, thus demonstrating a new strategy to construct a B,C,N-mixed π-system involving B=C and C=N bonds. Thermal isomerization of 2 gave C-borylimines ( 3), and diverse reactivity of 2 a towards several substrates, such as H+, F+, O2, S, Se, and isonitriles, allowed construction of boron-containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.
- Subjects
ISOMERIZATION; BIOCHEMICAL substrates; HETEROCYCLIC compounds; SYNTHETIC building materials; MOLECULAR dynamics; ISOMERISM
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 47, p14718
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201608994