2-Bromothiophene → 2-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490563Notes

Reaction equation

HRID 1490563 reaction equation
Brc1cccs1>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>CC1(C)OB(c2ccc(Br)s2)OC1(C)C

Participants

6

Reactant 1

HCID 138512-Bromothiophene

Product 1

HCID 117377972-(5-bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 96%

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
100 °C

Procedure

The general procedure A was followed using 2-bromothiophene (48.4 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 100 oC. 5t was obtained as orange oil (138.7 mg, 96 %) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v);

Sources & evidence

ORD record
ord-36a20897034c441f9bf4fb79b7aa05c4
Source dataset
Borylation dataset from Roche

Reaction notes

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