1-Tetralone → 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-one

HRID 1490933Notes

Reaction equation

HRID 1490933 reaction equation
O=C1CCCc2ccccc21>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.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2ccc3c(c2)C(=O)CCC3)OC1(C)C.CC1(C)OB(c2ccc3c(c2)CCCC3=O)OC1(C)C

Participants

7

Reactant 1

HCID 107241-Tetralone

Product 2

HCID 68473465HCID 68473465, compoundYield 20%HCID 713038396-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-oneYield 80%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

General procedure Dwas applied to 3,4-dihydronaphthalen-1(2H)-one15i(29mg, 0.2mmol). The reactionmixture was allowed to stand for 16hoursgiving a conversion of >99% (GC-MS) and 16iand 17iin a 80:20mixture (1H NMR spectrum).

Sources & evidence

ORD record
ord-f3741a9c10d54b95a8a57098ee379e4e
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…