Three-component reaction discovery enabled by mass spectrometry of self-assembled monolayers

Timothy J. Montavon, Jing Li, Jaime R. Cabrera-Pardo, Milan Mrksich*, Sergey A. Kozmin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Multicomponent reactions are employed extensively in many areas of organic chemistry. Despite significant progress, the discovery of such enabling transformations remains challenging. Here, we present the development of a parallel, label-free reaction-discovery platform that can be used in the identification of new multicomponent transformations. Our approach is based on parallel mass spectrometric screening of interfacial chemical reactions on arrays of self-assembled monolayers. This strategy enabled the identification of a simple organic phosphine that can catalyse a previously unknown condensation of siloxyalkynes, aldehydes and amines to produce 3-hydroxyamides with high efficiency and diastereoselectivity. The reaction was further optimized using solution-phase methods.

Original languageEnglish (US)
Pages (from-to)45-51
Number of pages7
JournalNature chemistry
Volume4
Issue number1
DOIs
StatePublished - Jan 2012

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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