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Nat Chem. 2013 May;5(5):423-7. doi: 10.1038/nchem.1612. Epub 2013 Mar 31.

Label-assisted mass spectrometry for the acceleration of reaction discovery and optimization.

Author information

1
Department of Chemistry (Chicago Tri-Institutional Centre for Chemical Methods and Library Development), University of Chicago, Chicago, Illinois 60637, USA.

Abstract

The identification of new reactions expands our knowledge of chemical reactivity and enables new synthetic applications. Accelerating the pace of this discovery process remains challenging. We describe a highly effective and simple platform for screening a large number of potential chemical reactions in order to discover and optimize previously unknown catalytic transformations, thereby revealing new chemical reactivity. Our strategy is based on labelling one of the reactants with a polyaromatic chemical tag, which selectively undergoes a photoionization/desorption process upon laser irradiation, without the assistance of an external matrix, and enables rapid mass spectrometric detection of any products originating from such labelled reactants in complex reaction mixtures without any chromatographic separation. This method was successfully used for high-throughput discovery and subsequent optimization of two previously unknown benzannulation reactions.

PMID:
23609094
PMCID:
PMC4512672
DOI:
10.1038/nchem.1612
[Indexed for MEDLINE]
Free PMC Article

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