157444-69-4Relevant academic research and scientific papers
Palladium-catalyzed α-arylation of zinc enolates of esters: Reaction conditions and substrate scope
Hama, Takuo,Ge, Shaozhong,Hartwig, John F.
, p. 8250 - 8266 (2013/09/24)
The intermolecular α-arylation of esters by palladium-catalyzed coupling of aryl bromides with zinc enolates of esters is reported. Reactions of three different types of zinc enolates have been developed. α-Arylation of esters occurs in high yields with i
Arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)]PdBr}
Hama, Takuo,Hartwig, John F.
supporting information; experimental part, p. 1545 - 1548 (2009/04/07)
Conditions for the coupling of bromoarenes with esters using a single base and catalyst with improved turnover numbers are described. These general conditions were made possible by using the Pd(l) catalyst {[P(f-Bu) 3]PdBr}2. Reactions of acetates, propionates, and isobutyrates are presented, and reactions of all three classes of esters on a 10 g scale are described.
Efficient synthesis of α-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates
Jorgensen, Morten,Lee, Sunwoo,Liu, Xiaoxiang,Wolkowski, Joanna P.,Hartwig, John F.
, p. 12557 - 12565 (2007/10/03)
A catalytic amount of Pd(dba)2 ligated by either carbene precursor N,N′-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium (1) or P(t-Bu)3 mediated the coupling of aryl halides and ester enolates to produce α-aryl esters in high yields at room temperature. The reaction was highly tolerant of functionalities and substitution patterns on the aryl halide. Improved protocols for the selective monoarylation of tert-butyl acetate and the efficient arylation of α,α-disubstituted esters were developed with LiNCy2 as base and P(t-Bu)3 as ligand. In addition, tert-butyl esters, such as those of Naproxen and Flurbiprofen, were prepared from tert-butyl propionate and aryl bromides in high yields in the presence of Pd(dba)2 and the hindered, saturated heterocyclic carbene ligand precursor.
