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- Title
Monobenzofused 1,4-Azaborines: Synthesis, Characterization, and Discovery of a Unique Coordination Mode.
- Authors
Xu, Senmiao; Haeffner, Fredrik; Li, Bo; Zakharov, Lev N.; Liu, Shih-Yuan
- Abstract
We report the first general synthesis of boronsubstituted monobenzofused 1,4-azaborines using ring-closing metathesis of an enamine-containing diene as a key synthetic strategy. As part of our investigations, we discovered that the BC3 moiety in a 1,4-azaborine can serve uniquely as a η²-L-type ligand. This functionality is exemplified by two k²-N-η²-BC Pt complexes of a boron-pyridyl-substituted monobenzofused-1,4-azaborine. Single-crystal X-ray diffraction analysis of the Pt complexes shows a strong structural contribution from the iminium resonance form of the monobenzofused-1,4-azaborine ligand. We also demonstrate that a palladium(0) complex supported by a 1,4-azaborine-based phosphine ligand can catalyze hydroboration of 1-buten-3-yne with unique selectivity. In view of the importance of arene-metal p-interactions in catalytic applications, this work should open new opportunities for ligand design involving the 1,4-azaborine motif as an arene substitute.
- Subjects
BENZOFURANS; METATHESIS reactions; CHEMICAL reactions; BORENIUM ions; PALLADIUM
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 26, p6795
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201403903