期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 124, 期 42, 页码 12557-12565出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja027643u
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资金
- NIGMS NIH HHS [GM58108] Funding Source: Medline
A catalytic amount of Pd(dba)(2) ligated by either carbene precursor NAr-bis(2,6-diisopropylphenyl)4,5-dihydroimidazolium (1) or P(t-Bu)(3) mediated the coupling of aryl halides and ester enolates to produce alpha-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 alpha,alpha-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.
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