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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. Below it: runs of this reaction that somebody published, with the conditions they used.

Mechanism written

A reaction of this kind

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

What it needs, and what it gives

Reaction class
Cross-coupling
Typical conditions
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.
Mass balance
balanced — the co-products are written out, not dropped
Mechanism
Sonogashira coupling (catalytic cycle), 4 steps

Typical conditions are what the literature ordinarily uses. The worked examples further down are what particular people actually ran, and the two do not always agree.

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.

  1. The metal inserts into the aryl-halide bond
  2. The base takes the alkyne's hydrogen
  3. The alkyne is carried to the metal
  4. The two groups are joined and the metal lets go

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

Read the Sonogashira coupling (catalytic cycle) mechanism

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

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>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

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)(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

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>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

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>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

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>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

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)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

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>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

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>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

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>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

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>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

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)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

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(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

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)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

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>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

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>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

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>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

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)(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

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)(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

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)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

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>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

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)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

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>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

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)(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.

Other classes

Buchwald–Hartwig amination

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

Suzuki–Miyaura coupling

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

Reduction

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

Deprotection

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

Oxidation

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

Reductive amination

Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.

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