铜铁共催化2-芳基丙烯酸酯的脱酯氧膦化反应
Deesterificative oxyphosphorylation of 2-aryl acrylates at Cu/Fe-cocatalyzed
作者：高明;王华斌;黄强;董凯凯;姬建新;易东;孙雅婧;
Author：
收稿日期： 年卷（期）页码：2019,34(01):-15-21
期刊名称：华西药学杂志
Journal Name：WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字：2-芳基丙烯酸酯;脱酯氧膦化;β-羰基膦酸酯;亚磷酸酯;铜;铁;共催化;氧气
Key words：
基金项目：
中文摘要
目的建立一种通过2-芳基丙烯酸酯的脱酯氧膦化反应构建β-羰基膦酸酯的新方法。方法在60℃、氧气条件下,以Cu Br2/Fe Cl3作催化剂,用三乙胺作碱、二甲基亚砜为溶剂,2-芳基丙烯酸酯和亚磷酸酯发生脱酯氧膦化反应4 h,以中等至较高的收率得到相应的目标产物。结果和结论合成了一系列β-羰基膦酸酯,结构经1HNMR、13CNMR和13PNMR表征。该反应具有良好的底物普适性和官能团耐受性。
参考文献
[1]Kenichi K,Kosaku T,Hiroshi K.Recent topics of the natural product synthesis by Horner-Wadsworth-Emmons reaction[J].Tetrahedron Lett,2018,59(7):568-582.
[2]Hou XM,Tang SF.An investigation on the structural diversification of metal phosphonates in varying combinations of phosphonate ligand,metal ions and auxiliary ligands[J].Inorg Chim Acta,2018,473:169-179.
[3]Mitchell LA,Holliday BJ.Polymeric materials for the separation of f-elements utilizing carbamoylmethylphosphine oxide chelating ligands[J].ACS Macro Lett,2016,5(10):1100-1103.
[4]Tang P,Zhang C,Chen,E,et al.MnⅢ-catalyzed phosphorylation of vinyl azides:The synthesis ofβ-keto phosphine oxides[J].Tetrahedron Lett,2017,58(22):2157-2161.
[5]Li L,Huang W,Chen L,et al.Silver-catalyzed oxidative C(sp3)-P bond formation through C-C and P-H bond cleavage[J].Angew Chem Int Ed,2017,56(35):10539-10544.
[6]Zhou P,Hu B,Li L,et al.Mn(OAc)3-promoted oxidative C(sp3)-P bond formation through C(sp2)-C(sp2)and P-H bond cleavage:Access to beta-Ketophosphonates[J].J Org Chem,2017,82(24):13268-13276.
[7]Caputo JA,Frenette LC,Zhao N,et al.General and efficient C-C bond forming photoredox catalysis with semiconductor quantum dots[J].J Am Chem Soc,2017,139(12):4250-4253.
[8]Heng J,Armido S.α-Aminoxy-acid-auxiliary-enabled intermolecular radicalγ-C(sp3)-H functionalization of ketones[J].Angew Chem Int Ed,2018,57(6):1692-1696.
[9]Yi D,Fu Q,Chen SY,et al.Copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen[J].Tetrahedron Lett,2017,58(21):2058-2061.
[10]Wei W,Ji JX.Catalytic and direct oxyphosphorylation of alkenes with dioxygen and H-Phosphonates leading toβ-ketophosphonates[J].Angew Chem Int Ed,2011,50(39):9097-9099.
[11]Fu Q,Yi D,Zhang ZJ,et al.Copper-catalyzed aerobic oxidative coupling of ketones with P(O)-H compounds leading toβ-ketophosphine oxides[J].Org Chem Front,2017,4(7):1385-1389.
[12]Liang W,Zhang ZJ,Yi D,et al.Copper-catalyzed direct oxyphosphorylation of enamides with P(O)-H compounds and dioxygen[J].Chin J Chem,2017,35(9):1378-1382.
【关闭】
