Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14795-14799Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507805
Keywords
acid catalysis; electrospray; mass spectrometry; protonation; reaction mechanisms
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Funding
- Air Force Office of Scientific Research through a Basic Research Initiative grant (AFOSR) [FA9550-12-1-0400]
- National Science Foundation under the CCI Center for Selective C-H Functionalization [CHE-1205646]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205646] Funding Source: National Science Foundation
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A Pomeranz-Fritsch synthesis of isoquinoline and Friedlander and Combes syntheses of substituted quinolines were conducted in charged microdroplets produced by an electrospray process at ambient temperature and atmospheric pressure. In the bulk phase, all of these reactions are known to take a long time ranging from several minutes to a few days and to require very high acid concentrations. In sharp contrast, the present report provides clear evidence that all of these reactions occur on the millisecond timescale in the charged microdroplets without the addition of any external acid. Decreasing the droplet size and increasing the charge of the droplet both strongly contribute to reaction rate acceleration, suggesting that the reaction occurs in a confined environment on the charged surface of the droplet.
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