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4-tert-Butyltoluene → 2-(5-(tert-butyl)-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490570
Notes
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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
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 73904-tert-Butyltoluene

Product 1

HCID 1223712302-(5-(tert-butyl)-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 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-benzodiazaboroleReagent

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
DOI
10.1021/jacs.5b05252

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 76001521
Bis(1,5-cyclooctadiene)dimethoxydiiridium
Catalyst
HCID 138539Cyclopentyl methyl etherSolvent