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Buchwald–Hartwig etherification

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

A reaction of this kind

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

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

Oc1ccccc1.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)=O>c1ccc(Oc

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

Oc1ccccc1.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)P1(=NC(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

Oc1ccccc1.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(C)(C)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

OCCCc1ccccc1.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.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

OCCCc1ccccc1.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.CC(C)(C)N=P(N1CCCC1

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

OCCCc1ccccc1.Brc1cccnc1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c1cccc2P(c1ccccc1)(c1ccccc1)->[Pd]1(Cl)<-Nc2ccccc2-c2ccccc21.CS(C)=O.CS(C)=O.C1CCC2=NCCCN2CC1.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

OCCCc1ccccc1.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(CC)P1(=NC(C)(C)C)N(C)CCCN1C.CS(C)=O.CS(C)=O>c1ccc(CCCO

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

Oc1ccccc1.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>c1ccc(Oc2cccnc2)cc1.B

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

OCCCc1ccccc1.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-c1c(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

Oc1ccccc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.CS(C)=O.CS(C)=O.CN1CCCN2CC

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

Oc1ccccc1.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.CN1CCCN2CCCN=C12

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

Oc1ccccc1.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.C1CCC2=NCCCN2CC1.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

OCCCc1ccccc1.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.C1CCC2=NCCCN2

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

OCCCc1ccccc1.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(=NC(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

OCCCc1ccccc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.CS(C)=O.CS(C)=O.C1CCC2=

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

OCCCc1ccccc1.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.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.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

OCCCc1ccccc1.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(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

Oc1ccccc1.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)P1(=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

Oc1ccccc1.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=P(N=P(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

OCCCc1ccccc1.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=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.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

Oc1ccccc1.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(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

Oc1ccccc1.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-c1c(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

OCCCc1ccccc1.Brc1cccnc1>CS(=O)(=O)O[Pd]1(<-Nc2ccccc2-c2ccccc21)<-P(c1ccccc1)(c1ccccc1)c1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.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

OCCCc1ccccc1.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=NCCCN2CC1.CS

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.