Suzuki–Miyaura 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 boron hands over its carbon, and the two groups on the metal join and leave together.

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

Read the Suzuki coupling (catalytic cycle) mechanism

What the engine will do with your structures

Suzuki 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. Usually run: 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.

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

How it is thought to work

What the engine will do with your structures

Suzuki coupling

Worked examples

Reading these records

Other classes

Buchwald–Hartwig amination

Reductive amination

Mizoroki–Heck reaction

Imidazole arylation

Buchwald–Hartwig etherification

Boc deprotection

Where to next

All classes

Search by structure

Mechanisms