Coupling Reaction - Coupling Types

Coupling Types

Coupling reactions include (not exhaustive):

Reaction year Reactant A Reactant B homo/cross catalyst remark
Wurtz reaction 1855 R-X sp³ R-X sp³ homo Na
Glaser coupling 1869 RC≡CH sp RC≡CH sp homo Cu O2 as H-acceptor
Ullmann reaction 1901 Ar-X sp² Ar-X sp² homo Cu high temperatures
Gomberg-Bachmann reaction 1924 Ar-H sp² Ar-N2X sp² homo requires base
Cadiot-Chodkiewicz coupling 1957 RC≡CH sp RC≡CX sp cross Cu requires base
Castro-Stephens coupling 1963 RC≡CH sp Ar-X sp² cross Cu
Gilman reagent coupling 1967 R2CuLi R-X cross
Cassar reaction 1970 Alkene sp² R-X sp³ cross Pd requires base
Kumada coupling 1972 Ar-MgBr sp², sp³ Ar-X sp² cross Pd or Ni
Heck reaction 1972 alkene sp² R-X sp² cross Pd requires base
Sonogashira coupling 1975 RC≡CH sp R-X sp³ sp² cross Pd and Cu requires base
Negishi coupling 1977 R-Zn-X sp³, sp², sp R-X sp³ sp² cross Pd or Ni
Stille cross coupling 1978 R-SnR3 sp³, sp², sp R-X sp³ sp² cross Pd
Suzuki reaction 1979 R-B(OR)2 sp² R-X sp³ sp² cross Pd requires base
Hiyama coupling 1988 R-SiR3 sp² R-X sp³ sp² cross Pd requires base
Buchwald-Hartwig reaction 1994 R2N-R SnR3 sp R-X sp² cross Pd N-C coupling, second generation free amine
Fukuyama coupling 1998 R-Zn-I sp3 RCO(SEt) sp2 cross Pd
Liebeskind–Srogl coupling 2000 R-B(OR)2 sp3, sp2 RCO(SEt) sp2 cross Pd requires CuTC
Coupling reaction overview. For references consult satellite pages

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