Research Article

Snap deconvolution: An informatics approach to high-throughput discovery of catalytic reactions

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Science  14 Jul 2017:
Vol. 357, Issue 6347, pp. 175-181
DOI: 10.1126/science.aan1568

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A triple search for coupling reactions

Coupling reactions are, in principle, good candidates for high-throughput discovery: Simply mix a diverse set of reagents and then look for products that combine two or three of their masses. In practice, however, numerous different products might have masses that are too similar to distinguish quickly. Troshin and Hartwig circumvented this problem by screening three pools of reagents in parallel that shared the same reactive functionality but differed in mass by carefully chosen increments. Specific products could then be identified in a noisy distribution by their distinctive expected mass differences across the three pools.

Science, this issue p. 175


We present an approach to multidimensional high-throughput discovery of catalytic coupling reactions that integrates molecular design with automated analysis and interpretation of mass spectral data. We simultaneously assessed the reactivity of three pools of compounds that shared the same functional groups (halides, boronic acids, alkenes, and alkynes, among other groups) but carried inactive substituents having specifically designed differences in masses. The substituents were chosen such that the products from any class of reaction in multiple reaction sets would have unique differences in masses, thus allowing simultaneous identification of the products of all transformations in a set of reactants. In this way, we easily distinguished the products of new reactions from noise and known couplings. Using this method, we discovered an alkyne hydroallylation and a nickel-catalyzed variant of alkyne diarylation.

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