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4-Fluorobenzaldehyde → 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

HRID 1490623
Notes
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Reaction equation

HRID 1490623 reaction equation
O=Cc1ccc(F)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)N.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.[Ir].[Ir]>CC1(C)OB(c2cc(C=O)ccc2F)OC1(C)C
ParticipantsConditionsSources & evidenceReaction notes

Participants

8

Reactant 1

HCID 680234-Fluorobenzaldehyde

Product 1

HCID 467380184-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeYield 80%

Reagents, catalysts & solvents 6

HCID 6385Tert-ButylamineReagentHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Sources & evidence

ORD record
ord-af5e395bf7674facb9c197d699dab730
Source dataset
Borylation dataset from Roche
DOI
10.1021/jacs.5b11683

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes