N-Triisopropylsilylpyrrole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole

HRID 1490507Notes

Reaction equation

HRID 1490507 reaction equation
CC(C)[Si](C(C)C)(C(C)C)n1cccc1>B1Oc2ccccc2O1.C1=CC2C=CC1C2.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CC(C)[Si](C(C)C)(C(C)C)n1ccc(B2OC(C)(C)C(C)(C)O2)c1

Participants

8

Reactant 1

HCID 145136N-Triisopropylsilylpyrrole

Product 1

HCID 114509243-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrroleYield 45%

Reagents, catalysts & solvents 6

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 8473NorbornadieneReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Prepared from N-(triisopropylsilyl)-1H-pyrrole (4g, 44.6 mg, 0.200 mmol, 1.00 equiv), catBH (48.0 mg, 0.400 mmol, 2.00 equiv), N,N,4-trimethylaniline (1f, 2.7 mg, 0.020 mmol, 0.10 equiv), norbornene (18.8 mg, 0.20 mmol, 1.00 equiv) and B(C6F5)3 (10.1 mg, 0.020 mmol, 0.10 equiv) according to GP 3. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 6g[S4] (31.0 mg, 45%) as a white solid.

Sources & evidence

ORD record
ord-a17137a9aad6418aa78cfde7c8f2ee9d
Source dataset
Borylation dataset from Roche

Reaction notes

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