Research Article

Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines

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Science  05 Apr 2019:
Vol. 364, Issue 6435, pp. 45-51
DOI: 10.1126/science.aaw4029

Amines emerge, as copper bides its time

Concurrent operation of two or more catalytic cycles requires a delicate balance of relative rates. Zhang et al. developed an amine synthesis in which allenes and nitriles are coupled under reductive conditions. A copper catalyst was charged with successively borylating the allene, coupling the intermediate to the nitrile, and then enantioselectively reducing that next intermediate to the amine. However, formation and reaction of the copper-boryl complex were too slow relative to a competing copper hydride. By adding an innovative delay cycle, the authors succeeded in keeping the fast-reacting hydride at bay until needed.

Science, this issue p. 45

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