N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Biphenyl

HRID 609029Notes

Reaction equation

HRID 609029 reaction equation
CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.O=C1NCCc2[nH]c(-c3ccnc(Br)c3)cc21>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>CN(C)c1ccc(-c2cc(-c3cc4c([nH]3)CCNC4=O)ccn2)cc1

Participants

9

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 145711761HCID 145711761, compound

Product 3

HCID 7095BiphenylHCID 60118251HCID 60118251, compoundHCID 145711761HCID 145711761, compound

Reagents, catalysts & solvents 4

HCID 178439025HCID 178439025, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 962WaterSolventHCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineOther

Workup

  1. additionAfter 22 hours the crude reactions were diluted with 3 x 1 uL 0.5 M AcOH in DMSO (containing PhPh as an internal standard). The reactions were mixed after each dispense operation.
  2. aliquotMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis.

Sources & evidence

ORD record
ord-cfd6f7e42b7c42db94c1de2f87072e0e
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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