A novel synthesis of stable 3H-pyrrolizine fused diazaborepin. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Li, Yujiao; Yan, Jiaying; Xiao, Shuzhang; Zhang, Bao; Lu, Futai; Cheng, Kai; Li, Dejiang; Feng, Yaqing; Zhang, Nuonuo
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3226
• Page End: 3230
• Publication Date: 2016-07-20
• Subjects: Diazaborepin -- Piperidinium acetate -- 3H-Pyrrolizine -- Borepin -- BF2 complex; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.052
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The stable 3 H -pyrrolizine fused diazaborepin have designed and synthesized. The structure of 3 H -pyrrolizine fused diazaborepin was a saddle shape backbone. Under piperidinium acetate, 'naked' diazaborepin was achieved in one step. Abstract: We have designed and synthesized the original example of stable 3 H -pyrrolizine fused diazaborepin using boron–amine (B–N) chemistry. 3 H -Pyrrolizine fused 'naked' diazaborepin was achieved by organocatalyst (piperidinium acetate) in modest yield. The structure of diazaborepin was a twisted backbone in saddle shape with torsion angels of more than 20° from its crystal and theoretical data. It had a larger stokes shift (>70 nm) than classical BODIPYs and the type of solvent had an effect on their fluorescence property.