Format

Send to

Choose Destination
See comment in PubMed Commons below
J Org Chem. 2013 Dec 6;78(23):11747-55. doi: 10.1021/jo401748d. Epub 2013 Nov 12.

Modification and unexpected reactivity of 2-borylbenzaldimines: acylated and silylated derivatives as well as dimeric compounds.

Author information

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität , Corrensstrasse 40, 48149 Münster, Germany.

Abstract

Various novel N-alkyl and N-benzyl 2-borylbenzaldimines 3 were prepared by condensation of 2-(dimesitylboryl)benzaldehyde (1) with amines. Further functionalization of compound 3e was possible by deprotonation and subsequent regioselective reaction with electrophiles to give compounds 4. Applying similar conditions to 3a led to the unexpected formation of hitherto unknown dimeric compounds (5 and 6). All structural types were fully characterized, including by X-ray diffraction (XRD). Furthermore, quantum chemical calculations on the SCS-MP2 and DFT levels gave insights into the reaction mechanisms and the stereoselectivity. The B/N bonding situation in these molecules was analyzed using Wiberg bond indices. Preliminary UV-vis and fluorescence measurements indicate that the substitution reaction leading to compounds 4 can be utilized to tune the photophysical properties of these compounds.

[PubMed]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Write to the Help Desk