Lithium diisopropylamide-potassium

Iodine-Mercury(II) oxide, 149 Lithium diisopropylamide-Potassium /-butoxide, 164 Molybdenum carbonyl, 194 Phenyliodine(III) diacetate, 242 Sulfuryl chloride, 284 Conjugate addition reactions Michael reactions Alumina, 14... 

Allyltriphenylsilane, 13 Diacetatobis(triphenylphosphine)-palladium(II), 91 Dichlorobis(triphenylphosphine)-palladium(II), 103 (3-Dimethylaminopropyl)triphenyl-phosphonium bromide, 119 Lithium diisopropylamide-Potassium r-butoxide, 164... 

Ethylenediamine, 157 Hexamethyldisilazane, 175, 331 Isopropylamine, 164 N-Lithioethylenediamine, 157, 200 Lithium amides, chiral, 159 Lithium 3-aminopropylamide, 157, 160 Lithium 3-aminopropylamide-Potas-sium /-butoxide, 160 Lithium dicyclohexylamide, 110 Lithium diisopropylamide, 106, 143, 148, 163, 188, 256, 257, 326 Lithium diisopropylamide-Hexa-methylphosphoric triamide, 143, 172 Lithium diisopropylamide-Potassium t-butoxide, 164... 

CLAISEN REARRANGEMENT Alkylaluminum halides. Lithium diisopropylamide. Potassium hydride. Sodium dithionite. Titanium(TV) chloride. Trifluoroacetic acid. Trimethylaluminum. 

The optional site selective metallation of fluorotoluenes158 with the superbasic mixture of butyllithium and potassium fert-butoxide has been applied to the synthesis of the anti-inflammatory and analgesic drug Flurbiprofen.171 3-Fluorotoluene is selectively metallated in the 4-position with LIC-KOR in THF at — 75 °C to afford, after reaction with fluorodimethoxyborane and hydrolysis, the corresponding boronic acid in 78% yield. A palladium-catalyzed coupling with bromobenzene gives the 2-fluoro-4-methylbiphenyl in 84% yield. This four-step sequence can also be contracted to a one-pot procedure with an overall yield of 79%. A double metallation with the superbasic mixture lithium diisopropylamide/potassium tert-butoxide (LIDA-KOR)172 173 is then required to produce flurbiprofen. 

The reaction of diiodomethane with a variety of bases (sodium hexamethyldisilazanide, lithium diisopropylamide, potassium triphenylmethanide, potassium iert-butoxide, potassium hydroxide under phase-transfer conditions, methyllithium) and alkenes does not afford iodocyclo-propanes. The thermal decomposition of diiodomethyl(phenyl)mercury in an alkene also does not result in the formation of iodocyclopropanes." ... 

Dihydro-2//-pyran and 2,6-dihydro-4-methyl-2//-pyran react with the lithium diisopropylamide/potassium tert-butoxide ("LIDA-KOR") mixture under p-eliminative ring opening to give lithium (Z)-penta-2,4-dien-l-olate and its 3-methyl derivative. 

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