DOI: 10.1126/science.1253647 ISSN:

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis

John C. Tellis, David N. Primer, Gary A. Molander
  • Multidisciplinary

A bright outlook for carbon coupling

In contemporary organic chemistry, it is straightforward to forge bonds between unsaturated carbons (i.e., carbons already engaged in double bonds) using cross-coupling catalysis. The protocol runs into some trouble, however, if one or both starting carbon centers are saturated (purely single-bonded). Tellis et al. and Zuo et al. independently found that combining a second, light-activated catalyst with a nickel cross-coupling catalyst could achieve selective coupling of saturated and unsaturated reagents (see the Perspective by Lloyd-Jones and Ball). Their methods rely on single-electron transfer from the light-activated catalyst to the saturated carbon, thereby enhancing its reactivity more effectively than the twoelectron mechanisms prevailing in traditional protocols.

Science , this issue p. 433 , p. 437 ; see also p. 381

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