N,N-Dibutylbenzamide → HCID 168436404, compound
Reaction equation
CCCCN(CCCC)C(=O)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)O.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].O=c1ccc2cccc(-c3ccc(-c4ccccn4)nc3)c2[nH]1.[Ir].[Ir].[K]>CCCCN(CCCC)C(=O)c1cccc(B2OC(C)(C)C(C)(C)O2)c1Participants
7
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 80 °C
Procedure
In an argon filled glove box, a 5.0 mL wheaton microreactor was charged with [Ir(cod)(OMe)]2 (1.98 mg, 1.5 mol%), L1 ligand (2.1 mg, 3.5 mol%), B2pin2 (50.8 mg, 1.0 equiv.), KOtBu (1.0 mg, 4.5 mol%) and dry THF (1.0 mL). The reaction mixture was stirred for 2 minutes at room temperature. To this mixture, N,N-dibutylbenzamide (46.7 mg, 0.2 mmol) was added. The microreactor was capped with a teflon pressure cap and placed into pre-heated aluminum block at 80 oC. The reaction mixture was stirred for 12 h. After completion (judged by GC/MS), THF was removed under reduced pressure and chromatographic separation with silica gel (15% ethylacetate in hexane) gave the meta-borylated product 4e (49.6 mg, 69%) as oil.
Sources & evidence
- ORD record
- ord-03012762915d4ccdbd8b6fdfaf5ceb80
- Source dataset
- Borylation dataset from Roche
Reaction notes
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