Sonogashira coupling

Recorded reactions filed under this class. The ones that carry a written procedure and an atom map are shown below as worked examples.

Mechanism written

A reaction of this kind

One of the recorded examples, drawn from its own reaction SMILES. Read this record

How it is thought to work

The metal inserts into the aryl-halide bond, the alkyne loses its hydrogen and is carried across, and the two groups join and leave together.

That is the pathway taught for the class, not a finding about any record on this page.

Read the Sonogashira coupling (catalytic cycle) mechanism

What the engine will do with your structures

Sonogashira coupling

A terminal alkyne is joined to an aromatic ring. The alkyne loses its hydrogen to a base, copper carries it to the palladium, and the two are joined there. Usually run: A palladium source, usually a copper salt, and an amine that serves as both base and solvent. Room temperature is often enough with an iodide.

Worked examples

A recorded reaction

Procedure (from the source record): The Mosquito was used to combine the source plate solutions by multi-aspiration of 250 nL of each of the four reaction components and then to dose the resulting reaction mixture (1 uL) into a 1536-well plate

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)(C1CCCCC1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(C)c(-c2c(C(C)C)cc(C(C)C)cc2C(C)C)c1P(C(C)(C)C)(C(C)(C)C)->[Pd]1(<-Nc2ccccc2-c2ccccc21)OS(C)(=O)=O.CS(C)=O.CS(C)=O.CN(C)C(=N…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)(C)P(C(C)(C)C)(C(C)(C)C)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.C1CCC2=NCCCN2CC1.CS(C)=O.CS(C)=O>CCCCc1ccc(C#Cc2cccnc…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1N1CCOCC1)(C12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)C12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3.…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(C1=CC=CC1[Fe]C1C=CC=C1P(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1.CS(C)=O.CS(C)=O.CN(C)C(=NC(…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c1cccc2P(c1ccccc1)(c1ccccc1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CC(C)(C)N=P(N1CC…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c(C(C)C)c1.CS(C)=O.CS(C)=O.CCN(CC)P1(=NC(…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.CS(C)=O.CS(C)=O.CC…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O.CS(C)=O.CCN(CC)P…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O.CS(C)=O.CN1CCCN2…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(C1=CC=CC1[Fe]C1C=CC=C1P(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1.CS(C)=O.CS(C)=O.CCN=P(N=P(N…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c(C(C)C)c1.CS(C)=O.CS(C)=O.CN1CCCN2CCCN=C…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C1=C(P(C2CCCCC2)(C2CCCCC2)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)C([Fe]C2C=CC=C2)C=C1)P(C(C)(C)C)C(C)(C)C.CS(C)=O.CS(C)=O.CC(…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c(C(C)C)c1.CS(C)=O.CS(C)=O.CCN(CC)P1(=NC(…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1N1CCOCC1)(C12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)C12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3.…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(OC)c(P(C23C[C@H]4C[C@@H](C2)C[C@@H](C3)C4)(C23C[C@H]4C[C@@H](C2)C[C@@H](C3)C4)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c1-…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(C)c(-c2c(C(C)C)cc(C(C)C)cc2C(C)C)c1P(C(C)(C)C)(C(C)(C)C)->[Pd]1(<-Nc2ccccc2-c2ccccc21)OS(C)(=O)=O.CS(C)=O.CS(C)=O.CCN=P(N=P…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)(C)P(C(C)(C)C)(C(C)(C)C)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CN(C)C(=NC(C)(C)C)N(C)C.CS(C)=O.CS(C)=O>CCCCc1ccc(C#C…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)(C)P(c1ccc(N)cc1)(C(C)(C)C)->[Pd]1(<-Nc2ccccc2-c2ccccc21)OS(C)(=O)=O.CS(C)=O.CS(C)=O.CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C.CS(C)=O.C…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c(C(C)C)c1.CS(C)=O.CS(C)=O.CCN=P(N=P(N(C)…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O.CS(C)=O.CC(C)(C)…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(<-Nc3ccccc3-c3ccccc32)OS(C)(=O)=O)c(C(C)C)c1.CS(C)=O.CS(C)=O.CCN=P(N=P(N(C)…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c1cccc2P(c1ccccc1)(c1ccccc1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CN(C)C(=NC(C)(C)…

A recorded reaction

C#Cc1ccc(CCCC)cc1.Brc1cccnc1>CC(C)(C)P(c1ccc(N)cc1)(C(C)(C)C)->[Pd]1(<-Nc2ccccc2-c2ccccc21)OS(C)(=O)=O.CS(C)=O.CS(C)=O.C1CCC2=NCCCN2CC1.CS(C)=O.CS(C)=O>CCCCc1cc…

A selection of the distinct transformations in this class. The rest are reachable through the Reaction Lab by searching your own structures.

Reading these records

Everything on a record page came from the source that published it. Conditions the source did not state are shown as not recorded, and no typical value is substituted for them. Yields are whatever was measured by whoever ran the experiment.

A reaction of this kind

How it is thought to work

What the engine will do with your structures

Sonogashira coupling

Worked examples

Reading these records

Other classes

Buchwald–Hartwig amination

Suzuki–Miyaura coupling

Reductive amination

Mizoroki–Heck reaction

Imidazole arylation

Buchwald–Hartwig etherification

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Mechanisms