N,N-Dimethylbenzamide → N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1490850Notes

Reaction equation

HRID 1490850 reaction equation
CN(C)C(=O)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.[Ir].[Ir]>CN(C)C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.CN(C)C(=O)c1cccc(B2OC(C)(C)C(C)(C)O2)c1

Participants

7

Reactant 1

HCID 11916N,N-Dimethylbenzamide

Product 2

HCID 2758657N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 29%HCID 4712678N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 20%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-8816e3252fb848849186a694310b8e50
Source dataset
Borylation dataset from Roche

Reaction notes

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