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Mizoroki–Heck reaction

Palladium inserts into the aryl-halide bond, the alkene inserts into the aryl-palladium bond, and the hydride is eliminated to leave the alkene where it started, now carrying the ring. 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 and a base, warm. The hydrogen and the palladium leave from the same face, and the conformation that arranges that with the two substituents apart is the lower one, so the trans alkene is what is isolated.
Mass balance
balanced — the co-products are written out, not dropped
Mechanism
Heck 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 alkene inserts into the aryl-metal bond, the metal takes back a hydrogen and leaves, and a base strips it so the metal can start again.

  1. The metal inserts into the aryl-halide bond
  2. The alkene inserts into the aryl-metal bond
  3. The metal takes a hydrogen back and lets go
  4. A base strips the acid and the metal starts again

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

Read the Heck 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

CCOC(=O)/C=C/c1ccccc1.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(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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)(C1CCCCC1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CC(C)(C)N=P(N1CCCC1)(N1CCC…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>COc1ccc(OC)c(P(C2CCCCC2)(C2CCCCC2)->[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…

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

CCOC(=O)/C=C/c1ccccc1.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.CN1CC…

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

CCOC(=O)/C=C/c1ccccc1.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…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)(C)P(C(C)(C)C)(C(C)(C)C)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CS(C)=O.CS(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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)(C)P(C1=CC=CC1[Fe]C1C=CC=C1P(C(C)(C)C)(C(C)(C)C)->[Pd]1(<-Nc2ccccc2-c2ccccc21)OS(C)(=O)=O)C(C)(C)C.CS(C)=O.CS(C)=O.CN(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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c1cccc2P(c1ccccc1)(c1ccccc1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CN1CCCN2CCCN…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)(C)P(C(C)(C)C)(C(C)(C)C)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CS(C)=O…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)(C1CCCCC1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CN(C)C(=NC(C)(C)C)N(C)C.CS…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC12CC3(C)OC(C)(CC(C)(O1)P3(c1ccccc1)->[Pd]1(<-Nc3ccccc3-c3ccccc31)OS(C)(=O)=O)O2.CS(C)=O.CS(C)=O.CCN(CC)P1(=NC(C)(C)C)N(C)CCCN…

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

CCOC(=O)/C=C/c1ccccc1.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)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

CCOC(=O)/C=C/c1ccccc1.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…

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

CCOC(=O)/C=C/c1ccccc1.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.C1CCC2=NCC…

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

CCOC(=O)/C=C/c1ccccc1.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…

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

CCOC(=O)/C=C/c1ccccc1.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…

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

CCOC(=O)/C=C/c1ccccc1.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)…

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

CCOC(=O)/C=C/c1ccccc1.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.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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.CS(C)=O.CS(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

CCOC(=O)/C=C/c1ccccc1.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.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

CCOC(=O)/C=C/c1ccccc1.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.C1CCC2=NCC…

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

CCOC(=O)/C=C/c1ccccc1.Brc1cccnc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)(C1CCCCC1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.CN1CCCN2CCCN=C12.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

CCOC(=O)/C=C/c1ccccc1.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=…

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

CCOC(=O)/C=C/c1ccccc1.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…

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

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Reductive amination

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

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