N-Methylbenzamide → N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1491052Notes

Reaction equation

HRID 1491052 reaction equation
CNC(=O)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(-c2ccccn2)nc1>CNC(=O)c1ccccc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 11954N-Methylbenzamide

Product 1

HCID 69218561N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 0%

Reagents, catalysts & solvents 4

HCID 14742,2'-BipyridineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 2:1) as the eluent.

Sources & evidence

ORD record
ord-ecb1fa564c574c269daf0952df1a6889
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…