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

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.

SUBMITTER: Montavon TJ 

PROVIDER: S-EPMC3243075 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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

Montavon Timothy J TJ   Li Jing J   Cabrera-Pardo Jaime R JR   Mrksich Milan M   Kozmin Sergey A SA  

Nature chemistry 20111204 1

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  ...[more]