Palladium-catalyzed α-arylation of esters with chloroarenes

Palladium-catalyzed α-arylation of esters with chloroarenes
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DOI:
10.1021/ol800258u
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发表时间:
2008-04-17
期刊:
影响因子:
5.2
通讯作者:
Hartwig, John F.
Hartwig, John F.
中科院分区:
化学1区
文献类型:
--
作者:
Hama, Takuo;Hartwig, John F.

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报道了钯催化的酯与氯代芳烃的α-芳基化反应。氯代芳烃与丙酸叔丁酯和异丁酸甲酯的烯醇化钠的反应在0.2- 1mol%的{[P(t-Bu)(3)]PdBr}(2)或Pd(dba)(2)和P(t-Bu)(3)的组合作为催化剂时以高产率发生。氯代芳烃与乙酸叔丁酯的Reformatsky试剂的反应是最具挑战性的,但对于氯苯和贫电子氯代芳烃,在1 mol %的Pd(dba)(2)和五苯基二茂铁基二叔丁基膦(Q-phos)催化下发生高产率。
Palladium-catalyzed alpha-arylations of esters with chloroarenes are reported. The reactions of chloroarenes with the sodium enolates of tertbutyl proplonate and methyl isobutyrate occur in high yields with 0.2-1 mol % of {[P(t-Bu)(3)]PdBr}(2) or the combination of Pd(dba)(2) and P(t-Bu)(3) as catalyst. The reactions of chloroarenes with the Reformatsky reagent of tert-butyl acetate were most challenging but occurred in high yields for chlorobenzene and electron-poor chloroarenes catalyzed by 1 mol % of Pd(dba)(2) and pentaphenylferrocenyl di-tert-butylphosphine (Q-phos).