4-tert-Butyltoluene → 1799485-26-9

HRID 1490570Notes

Reaction equation

HRID 1490570 reaction equation
Cc1ccc(C(C)(C)C)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>Cc1ccc(C(C)(C)C)cc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 73904-tert-Butyltoluene

Product 1

HCID 1223712301799485-26-9Yield 44%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
125 °C

Procedure

The general procedure A was followed using 1-(tert-butyl)-4-chlorobenzene (84.2 ul, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 125 oC. The 1H NMR conversion was 46%. 5ad was obtained as white solid (60.1 mg, 44%) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v). m.p.: 70-72 oC.

Sources & evidence

ORD record
ord-7fa3e0e65e7842b7a24def4d2d54161a
Source dataset
Borylation dataset from Roche

Reaction notes

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