Jump to main content
Jump to site search

Issue 1, 2015
Previous Article Next Article

Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates

Author affiliations

Abstract

Complex chemical reactions can occur in electrosprayed droplets on the millisecond time scale. The Hantzsch synthesis of 1,4-dihydropyridines was studied in this way using on-line mass spectral analysis to optimize conditions and characterize the product mixture. Changing the distance between the nanospray source and the MS inlet allowed exploration of reaction progress as a function of droplet time-of-flight. Desolvation of the charged microdroplets is associated with transformation from starting material to intermediates and eventually to product as the distance is increased. Results of the on-line experiments require a termination step that discontinuously completes the desolvation process and allows the generated gaseous ions to be used to characterize the state of the system at a particular time. The intermediates seen correspond to those known to occur in the bulk solution-phase reaction. Off-line collection of the sprayed reaction mixture allowed the recovery of 250 mg h−1 of desired reaction product from a single sprayer, permitting characterization by NMR and other standard methods. A thin film version of the accelerated reaction is described and it could be controlled through the temperature of the collection surface.

Graphical abstract: Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates

Back to tab navigation

Supplementary files

Article information


Submitted
11 Aug 2014
Accepted
28 Aug 2014
First published
09 Sep 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 397-401
Article type
Edge Article
Author version available

Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates

R. M. Bain, C. J. Pulliam and R. G. Cooks, Chem. Sci., 2015, 6, 397
DOI: 10.1039/C4SC02436B

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements