Number AL-106
PRODUCT NO. D10,620-8
These ethers are stable to alkali, organolithium and Grignard
reagents, Red-Al®, lithium aluminum hydride, acetic anhy-
dride, and chromium trioxide oxidations, yet
Resembles Toluene in physical properties
– Bromo and lodo Grignards tend to be more soluble in 2-MeTHF
where as chloro Grignard reagents tend to be less soluble
• Forms an azeotrope rich with water
electron-deficient pyrimidine
ring by the isopropyl Grignard reagent.
Finally, the ligand also allows for the clean and direct addition of
Grignard reagents to aryl acid chlorides to give the corresponding
for convenient and
safe handling of air- and moisture-sensitive materials (e.g.,
organolithium and Grignard solutions) that are packaged in Aldrich
Sure/Seal‰ bottles. The valve cap, when equipped with a
performed on the oxidative addition
of aryl halides with Pd(0) and subsequent coupling of Grignard
reagents. However, deficiencies in these previous examples include
high catalyst loadings, high temperatures
of Rieke® Organozinc Reagents that are stable as solutions in tetrahydrofuran.
These reagents have different reactivity and selectivity properties than the analogous Grignard Reagents, and are employed in
• Addition of β-dicarbonyl enolates to dienes
• Coupling of aryl and alkyl halides with
Grignard reagents
Ph
P
P
Ph
Ph
Ph
261947
dppb 7688-25-7 426.47 X X X X X • Lactonization of unsaturated
addition of Grignard reagents to unsaturated carbonyl
compounds.47 Prior to this group’s research, only meager
selectivities had been observed in the conjugate addition of
Grignard reagents, which stands
dimethylsilanol reagent, (N-Boc-2-pyrrolyl)-
dimethylsilanol, which has been successfully employed in Pd-catalyzed cross-coupling
reactions. Dimethylsilanols have recently emerged as attractive reagents for facile
Scheme 4, Parts (a) and (b)). In 2014, Li’s
group showed that the direct addition of alkyl Grignard reagents to
perfluoroarenes was also possible (Scheme 4, Part (c)).25 More recently,
Wu’s team developed