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1,3,5-Trimethoxybenzene → 4,4,5,5-Tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolane

HRID 1490572
Notes
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Reaction equation

HRID 1490572 reaction equation
COc1cc(OC)cc(OC)c1>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>COc1cc(OC)c(B2OC(C)(C)C(C)(C)O2)c(OC)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 693011,3,5-Trimethoxybenzene

Product 1

HCID 219239274,4,5,5-Tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolaneYield 20%

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)dimethoxydiiridium

Conditions

Temperature
150 °C

Procedure

The general procedure A was followed using 1,3,5-trimethoxybenzene (84.1 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 24 hours at 150 oC. The 1H NMR conversion was 21%. 5af was obtained as white solid (30.1 mg, 20%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 114-116 oC.

Sources & evidence

ORD record
ord-3b44e04ef3134bc5ba0999b39d644837
Source dataset
Borylation dataset from Roche
DOI
10.1021/jacs.5b05252

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
Catalyst
HCID 138539Cyclopentyl methyl etherSolvent