Electrochemically Driven Cross-Electrophile Coupling of Alkyl Halides

Kimberly See and Song Lin describe electrochemically driven cross-electrophile coupling of alkyl halides.

Carbon–carbon bonds are key structural units in organic molecules. Thus, a tremendous effort has been dedicated to studying their formation. Transition-metal-catalyzed cross-coupling reactions are among the most reliable approaches for the formation of C–C bonds in organic synthesis. To avoid synthetic steps to preform organometallic reagents as well as stability and functional-group-tolerance issues that are commonly associated with these nucleophiles, cross-electrophile coupling (XEC) of organic halides has drawn substantial  attention in the last decade as a methodology for achieving C–C bond formations. However, despite great advances in this area, the selective XEC of two alkyl halides to construct C(sp3)–C(sp3) bonds has remained elusive.
Harnessing electrochemistry to solve challenging problems in organic synthesis has been an overarching goal of Professor Song Lin’s research program at Cornell University (USA). Here, he describes the results of a collaborative effort with the group of Professor Kimberly See from Caltech (USA).

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