A Generalized Picture of C–C Cross-Coupling

2017/07/17 by Michael Busch, Matthew D. Wodrich, Clémence Corminbœuf · 1 citation
Chemistry · #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods #Cyclopropane Reaction Mechanisms

paper · pdf · doi:10.1021/acscatal.7b01415

openalex publication_date 2017/07/17 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04

Abstract

Transition metal catalyzed cross-coupling reactions occupy a privileged position in chemistry because of their ability to link myriad functional groups. The numerous variants of this reaction types (e.g., Suzuki, Kumada, Negishi, etc.) differ in the transmetallation agent used to transfer “R” groups onto the catalyst. While understanding any single variant (e.g., Suzuki coupling) can be accomplished through direct analysis of the catalytic cycle, a comprehensive picture that illustrates the interrelationships between the different types of cross-coupling reactions remains absent. Here, using a newly developed tool built upon a three-dimensional volcano plot we create a generalized thermodynamic picture of C-C cross-coupling reactions. This “cross-coupling” genome not only facilitates better understanding of catalytic behavior, but also outlines strategies for developing new reaction protocols through the manipulation of easily computed descriptor variables.

Citations

• Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
• The Mechanisms of the Stille Reaction
• Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism
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• Linear scaling relationships and volcano plots in homogeneous catalysis – revisiting the Suzuki reaction
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• The Stille Reaction, 38 Years Later

Cited by

• Clémence Corminboeuf [wikipedia]