Cross-Coupling Reactions
Every named cross-coupling reaction from Cross-Coupling Reactions: Mechanisms and Examples — catalytic cycle, general scheme, and every worked example, organized as one page per reaction.
Cross-coupling reactions are foundational in synthetic chemistry: the metal-catalyzed union of an organic electrophile — typically an aryl or vinyl halide — with an organometallic nucleophile to form a new carbon–carbon or carbon–heteroatom bond. They underpin the synthesis of pharmaceuticals, agrochemicals, natural products, and organic materials, and three of the chemists who developed the field — Richard Heck, Ei-ichi Negishi, and Akira Suzuki — shared the 2010 Nobel Prize in Chemistry for this work.
Each reaction below has its own page: what it is, its step-by-step catalytic cycle, the general reaction scheme, every worked example from the book with its original literature source, and links to related reactions.
Browse by reaction name
Buchwald-Hartwig Coupling
Pd-catalyzed C–N (and C–O) coupling for aryl amines
Cadiot-Chodkiewicz Coupling
Cu(I)-catalyzed unsymmetrical diyne synthesis
Chan-Evans-Lam Cross-Coupling
Cu-mediated C–N/C–O coupling of boronic acids under mild, base-free conditions
Fukuyama Cross-Coupling
Pd-catalyzed ketone synthesis from thioesters and organozincs
Fukuyama Reduction
Pd-catalyzed reduction of thioesters to aldehydes
Eglinton Reaction
Cu(II)-mediated oxidative homocoupling of terminal alkynes
Glaser-Eglinton-Hay Coupling
Catalytic Cu(I)/O2 oxidative alkyne homocoupling
Heck Cross-Coupling
Pd-catalyzed coupling of aryl/vinyl halides with alkenes
Hiyama Cross-Coupling
Pd-catalyzed, fluoride-activated coupling of organosilanes
Hiyama-Denmark Cross-Coupling
Fluoride-free silanol coupling
Kumada Cross-Coupling
Ni/Pd-catalyzed coupling of Grignard reagents
Liebeskind-Srogl Cross-Coupling
Cu(I)-assisted, base-free coupling of thioesters/thioethers with boronic acids
Miyaura Borylation
Pd-catalyzed synthesis of aryl/vinyl boronates from B2pin2
Negishi Cross-Coupling
Pd/Ni-catalyzed coupling of organozinc reagents
Nozaki-Hiyama-Kishi Cross-Coupling
Cr-mediated, Ni/Pd-catalyzed addition of organohalides to aldehydes
Sonogashira Cross-Coupling
Pd/Cu dual-catalyzed coupling of terminal alkynes
Stille Cross-Coupling
Pd-catalyzed, base-free coupling of organostannanes
Carbonylative Stille Coupling
Stille coupling under CO to give ketones
Suzuki Cross-Coupling
Pd-catalyzed coupling of boronic acids/esters — the most widely used cross-coupling
Ullmann Aryl-Aryl Coupling
Cu-mediated symmetric biaryl synthesis
Ullmann Coupling
Cu-catalyzed C–N/C–O/C–S coupling (the Ullmann condensation / Goldberg reaction)
Cross-Coupling Reactions: Mechanisms and Examples
All 21 reactions on this page are drawn from the book — organized by reaction name, with a clear description of each catalytic cycle and real examples from the primary literature.