Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 2-N,N-diisopropylaminophenylboronate derivatives

Coghlan, S.W.; Giles, R.L.; Howard, J.A.K.; Patrick, L.G.F.; Probert, M.R.; Smith, G.E.; Whiting, A.

Abstract

Directed ortho-metallation is used to introduce a boron function into N,N-diisopropylbenzamide,. resulting in the formation of both borinate and boronate derivatives. N,N-Diisopropylbenzamide ortho-boronate pinacol ester can be reduced with sodium borohydride-TMSCl resulting in N,N-diisopropylbenzylamino ortho-boronic acid. X-ray crystallography and B-11 NMR of this compound clearly shows that the hindered isopropylamino groups are sufficient to prevent B-N intramolecular coordination, which contrasts with NN-dimethylbenzylamino ortho-boronic acid. (c) 2005 Elsevier B.V. All rights reserved.

Citation

Coghlan, S., Giles, R., Howard, J., Patrick, L., Probert, M., Smith, G., & Whiting, A. (2005). Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 2-N,N-diisopropylaminophenylboronate derivatives. Journal of Organometallic Chemistry, 690(21-22), 4784-4793

• Journal Article Type: Article
• Publication Date: 2005-11
• Journal: Journal of Organometallic Chemistry
• Print ISSN: 0022-328X
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 690
• Issue: 21-22
• Pages: 4784-4793
• Public URL: https://durham-repository.worktribe.com/output/1595242