(Ethylthio)benzene → 2-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491130

Reaction equation

HRID 1491130 reaction equation
CCSc1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CCSc1ccccc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 12144(Ethylthio)benzene

Product 1

HCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 72%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

Ligand 3f: The mixture of product (95 mg, 72% yield, ortho/meta + para = >30); ortho-borylated product 4b was obtained by further purification of the crude mixture by GPC (89 mg, 67% yield), white solid (mp. 48-50 oC)

Sources & evidence

ORD record
ord-b26c7059a55f4ed08e56318eb7eb563c
Source dataset
Borylation dataset from Roche

Linked notes

Loading…