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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490960Generated: October 30, 2026

HCID 791728, compound → HCID 178457695, compound

https://huagongshe.com/reaction/1490960

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 791728HCID 791728—
ReagentBis(pinacolato)diboraneHCID 2733548—
Reagent8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-oneHCID 164681385—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
CatalystPotassium tert-butoxideHCID 86639980—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178457695HCID 17845769596%

Reaction Conditions

Temperature80 °C

Reaction Steps

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, 4-fluoro-N,N-diisopropylbenzamide (44.7 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 (12 % ethyl acetate in hexane as eluent) gave the meta-borylated product 6m (67.1 mg, 96%) as off white solid.

Provenance & Evidence

DOI10.1002/anie.201809929
Source datasetBorylation dataset from Roche
ORD IDord-aab6a51f01b94e668950eb8d922abcb7
Source noteBorylation dataset from Roche