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Abstract
Catalytic carbon–carbon bond formation based on cross-coupling reactions plays a central role in the production of natural products, pharmaceuticals, agrochemicals and organic materials. Coupling reactions of a variety of organometallic reagents and organic halides have changed the face of modern synthetic chemistry. However, the high reactivity and poor selectivity of common organolithium reagents have largely prohibited their use as a viable partner in direct catalytic cross-coupling. Here we report that in the presence of a Pd-phosphine catalyst, a wide range of alkyl-, aryl- and heteroaryl-lithium reagents undergo selective cross-coupling with aryl- and alkenyl-bromides. The process proceeds quickly under mild conditions (room temperature) and avoids the notorious lithium halogen exchange and homocoupling. The preparation of key alkyl-, aryl- and heterobiaryl intermediates reported here highlights the potential of these cross-coupling reactions for medicinal chemistry and material science. A general and selective palladium-catalysed cross-coupling of aryl- and alkenyl-bromides with a wide range of alkyl-, aryl- and heteroaryl-lithium reagents is reported. The process proceeds quickly at room temperature, and avoids the notorious lithium–halogen exchange and homocoupling side-reactions commonly associated with these extremely reactive organometallic compounds.Cite this article
Giannerini, M., Fañanás-Mastral, M. & Feringa, B. Direct catalytic cross-coupling of organolithium compounds. Nature Chem 5, 667–672 (2013). https://doi.org/10.1038/nchem.1678 