PerspectiveOrganic Chemistry

When two reactions become one

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Science  01 Jan 2016:
Vol. 351, Issue 6268, pp. 26-27
DOI: 10.1126/science.aad8698

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Summary

Organoboron compounds are among the most widely used reagents in organic synthesis and underpin many of the most frequently practiced and important reactions in synthetic organic chemistry (1). These reactions are based on specific mechanistic events that are distinctive to the reaction class. Catalytic processes are usually driven by transmetallation to transition metal complexes (passing a ligand from boron to the metal), whereas stoichiometric processes are based on metallate rearrangement mechanisms—ligands undergoing redistribution around a boron center—initiated by an incoming nucleophile. On page 70 of this issue, Zhang et al. (2) report an alternative transmetallation process that harmoniously merges these usually independent mechanisms, and they demonstrate its application within a multicomponent catalytic reaction that generates specific chiral products.

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