Suzuki–Miyaura coupling

Palladium inserts into the aryl-halide bond, the boron hands its carbon to the metal, and the two organic groups are joined as the metal lets go. 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, in aqueous or alcoholic solvent, warm. The base is not optional: the boron will not give up its carbon without it.
Mass balance: balanced — the co-products are written out, not dropped
Mechanism: Suzuki coupling (catalytic cycle), 3 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 boron hands over its carbon, and the two groups on the metal join and leave together.

The metal inserts into the aryl-halide bond
The boron hands its carbon to the metal
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 Suzuki coupling (catalytic cycle) mechanism

Worked examples

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.Cc1cc(C)c(B(O)O)c(C)c1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.COc1ccc(OC)c(P(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2cc(C(F)(…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccc(C(F)(F)F)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.O=C(O)c1cccc(P(c2cccc(C(F)(F)F)c2)c2cccc(C(F)(F)F)c2)…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CCCCP(C(C)(C)C)C(C)(C)C.O=P([O-])([O-])[O-].[K+].[K+]…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CN(C)c1cccc(N(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=P(…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CCCCCCCCP(CCCCCCCC)CCCCCCCC.O=P([O-])([O-])[O-].[K+].…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccc(C(F)(F)F)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.N#Cc1ccccc1P(c1ccccc1)c1ccccc1.O=P([O-])([O-])[O-].[K…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.Cc1cc(C)c(P(c2c(C)cc(C)cc2C)C2CCCC2)c(C)c1.O=P([O-])(…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.c1ccc(CP(Cc2ccccc2)Cc2ccccc2)cc1.O=P([O-])([O-])[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

CC1(C)OB(c2cnn(Cc3ccccc3)c2)OC1(C)C.O.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.CN(C)C(=NC(C)(C)C)N(C…

A recorded reaction

CC1(C)OB(c2cnn(Cc3ccccc3)c2)OC1(C)C.O.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc1…

A recorded reaction

CC1(C)OB(c2cnn(Cc3ccccc3)c2)OC1(C)C.O.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…

A recorded reaction

CC1(C)OB(c2cnn(Cc3ccccc3)c2)OC1(C)C.O.Brc1cccnc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)(C1CCCCC1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.C1CCC2=NCC…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.CCOC(=O)c1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.c1ccc(P(c2ccccc2)C2CCCCC2)cc1.O=P([O-])([O-])[O-].[K+…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccc(C(F)(F)F)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.Cc1ccccc1-c1ccccc1P(C(C)(C)C)C(C)(C)C.O=P([O-])([O-])…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)(C)P(C1CCCCC1)C1CCCCC1.O=P([O-])([O-])[O-].[K+].[K+].[K+].…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccc(C(F)(F)F)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.c1ccc(P(c2ccccc2)C2CCCCC2)cc1.O=P([O-])([O-])[O-].[K+…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.C1=Cc2ccccc2C(P(c2ccccc2)c2ccccc2)c2ccccc21.O=P([O-])([O-])[O-]…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.Cc1cc(C)c(B(O)O)c(C)c1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CP(C)C.O=P([O-])([O-])[O-].[K+].[K+].[K+].C1COCCO1>COc…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)(C)P(C1CCCCC1)C(C)(C)C.O=P([O-])([O-])[O-].[K+].…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)(C)c1cc(P(CC2CCCC2)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc(C(C)(C)…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.CCOC(=O)c1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)P(C(C)C)C(C)C.O=P([O-])([O-])[O-].[K+].[K+].[K+]…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.c1ccc(CP(Cc2ccccc2)Cc2ccccc2)cc1.O=P([O-])([O-])[O-].[K+].[K+].…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)CP(CC(C)C)CC(C)C.O=P([O-])([O-])[O-].[K+].[K+].[…

A recorded reaction

Procedure (from the source record): pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

FC(F)(F)c1ccc(Cl)cc1.COc1ccc(B(O)O)cc1>C1COCCO1.O.C1COCCO1.C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni].C1COCCO1.CC(C)(C)c1cc(P(c2cc(C(C)(C)C)cc(C(C)(C)C)c2)C2CCCCC2)…

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

What it needs, and what it gives

How it is thought to work

Worked examples

Reading these records

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