Redox reactions of small organic molecules using ball milling and piezoelectric materials - Science Magazine

Redox catalysis in a ball mill

Mixing solid reactants in a ball mill is a promising means of avoiding the copious solvent waste associated with most chemical syntheses. Kubota et al. now report that adding a piezoelectric catalyst to the mix can promote bond formation through apparent electron transfer cycles (see the Perspective by Xia and Wang). Specifically, barium titanate activates aryl diazonium salts toward borylation and coupling with heterocycles in a manner reminiscent of solutionphase photoredox catalysis. The reactions are insensitive to air and were demonstrated up to gram scale.

Science, this issue p. 1500; see also p. 1451

Abstract

Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be developed through the piezoelectric effect. Here, we report that agitation of piezoelectric materials via ball milling reduces aryl diazonium salts. This mechanoredox system can be applied to arylation and borylation reactions under mechanochemical conditions.

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Redox reactions of small organic molecules using ball milling and piezoelectric materials - Science Magazine
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