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What is a cross-coupling? An argument for a universal definition

Reimann, Christopher E. and Kim, Kelly E. and Rand, Alexander W. and Moghadam, Farbod A. and Stoltz, Brian M. (2023) What is a cross-coupling? An argument for a universal definition. Tetrahedron, 130 . Art. No. 133176. ISSN 0040-4020. PMCID PMC9878734. doi:10.1016/j.tet.2022.133176.

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Despite amazing advances in cross-coupling technologies over the past several decades, there is not a consistent definition of what a cross-coupling reaction is. Often, definitions rely on comparison to “traditional” palladium-catalyzed cross-couplings pioneered in the 1970s by chemists such as Suzuki, Negishi, and Heck. While these reactions provide a basis for a cross-coupling definition, they do not define this type of transformation, originally described by Linstead almost 20 years prior. Rather than modify and compartmentalize modern transformations to categorize them into either a synthetic or mechanistic definition, we make an argument for broadening the cross-coupling definition to the union of two distinct molecular entities in a covalent-bond-forming process, to encourage discussion around exploring novel reactivity and disconnections. In addition to making a case for a universal cross-coupling definition, we cite specific examples of reactions that break the mold of prior cross-coupling definitions. We believe this perspective will stimulate dialog around what it means to be a cross-coupling and in turn inspire future developments within this field.

Item Type:Article
Related URLs:
URLURL TypeDescription
Reimann, Christopher E.0000-0003-3274-7590
Kim, Kelly E.0000-0002-4132-2474
Rand, Alexander W.0000-0002-7099-5870
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:This work was supported by the NIH under NIH-NIGMS (R01GM080269 and R35GM145239), the Center for Selective C–H Functionalization (CCHF), and the Heritage Medical Research Institute Investigator Program. We thank Professor Scott E. Denmark (UIUC) for helpful discussions.
Group:Heritage Medical Research Institute
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Heritage Medical Research InstituteUNSPECIFIED
PubMed Central ID:PMC9878734
Record Number:CaltechAUTHORS:20230203-890564800.1
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:119001
Deposited By: Research Services Depository
Deposited On:24 Feb 2023 16:32
Last Modified:24 Feb 2023 16:32

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