Cross-coupling reaction

A reaction that joins two molecular fragments, commonly by forming a carbon–carbon bond with a transition-metal catalyst. Many named variants use an organometallic reagent and an organic electrophile.

Oxidative addition: An organometallic step in which a metal inserts into a bond, increasing its oxidation state and coordination number. It commonly activates the organic electrophile at the start of a cross-coupling cycle.
Suzuki reaction: A palladium- or nickel-catalyzed coupling of organoboron compounds with organic electrophiles. Its organoboron partners make it a widely used route to biaryl and related bonds.
Organometallic chemistry: The study of compounds containing bonds between carbon and metals, and their reactions. Many cross-couplings rely on organometallic intermediates or reagents to deliver one fragment.
Richard F. Heck: An American chemist whose palladium-catalyzed alkene arylation became the Mizoroki–Heck reaction. His work established a major catalytic route for coupling aryl halides with alkenes.
Direct C–H functionalization: A strategy that transforms a carbon–hydrogen bond directly into a new bond without first installing a leaving group. It can avoid preparing the prefunctionalized electrophiles often required in cross-coupling.
Transmetalation: Transfer of an organic group from one metal or metalloid center to another metal center. It often brings the coupling partner onto the catalyst after electrophile activation.
Mizoroki–Heck reaction: A palladium-catalyzed reaction that couples an aryl or vinyl halide with an alkene. It joins fragments by adding an aryl or vinyl group across an alkene framework.
Organic halide: An organic compound in which a halogen atom is bonded to carbon. A carbon–halogen bond often identifies the electrophile that enters the catalytic cycle.
Ei-ichi Negishi: A Japanese-American chemist known for developing organozinc-based cross-coupling reactions. His research demonstrated the broad synthetic value of organozinc coupling partners.
Photoredox catalysis: Catalysis that uses light-absorbing molecules to drive single-electron transfer reactions. Photoredox methods can form bonds through radical pathways rather than conventional two-electron metal cycles.

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