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Bis(β-diketiminato) Lanthanide(Ⅱ) Complexes-Catalyzed Hydro-phosphonylation of Aldehydes/Ketones and Diethyl Phosphite
Received date: 2016-03-03
Revised date: 2016-04-27
Online published: 2016-05-06
Supported by
Project supported by the National Natural Science Foundation of China (No.21372171).
The hydrophosphonylation of aldehydes/ketones was explored by use of seven bis(β-diketiminato) lanthanide(Ⅱ) complexes[Eu(L2,6-ipr2)2·CH3C6H5, L2,6-ipr2=[N(2,6-iPr2C6H3)C(Me)]2CH- (1); Eu(L2,6-Me2)2(THF), L2,6-Me2=[N(2,6-Me2C6H3)C(Me)]2CH- (2); Eu(L2,4,6-Me3)2(THF), L2,4,6-Me3=[N(2,4,6-Me3C6H2)C(Me)]2CH- (3); Eu(L2,6-ipr2Ph)2, L2,6-ipr2Ph=[(2,6-iPr2C6H3)NC(Me)CHC(Me)N(C6H5)]-(4); Sm(L2,6-ipr2)2·CH3C6H5 (5); Yb(L2,6-ipr2Ph)2 (6); Yb(L2-Me)2(THF), L2-Me=[N(2-MeC6H4)C(Me)]2CH- (7)] as the catalysts. All complexes were found to be able to catalyze the hydrophosphonylation between aromatic or heterecycle aldehyde and diethyl phosphite with high activity under wild conditions. All the reactions gave the products in 90%~99% yields using 0.08 mol% of complex 7 at 25℃ under solvent-free. The catalyst activity was found to depend on the β-diketiminato ligands with the sequence of L2,6-Me22,4,6-Me32,6-ipr2≈L2,6-ipr2Ph. This catalyst system showed a wide scope of aldehydes. Besides, bis(β-diketiminato) lanthanide(Ⅱ) complexes could also efficiently catalyze the hy-drophosphonylation of unactive ketones with diethyl phosphite and showed a good substrate scope.
Liu Qianqian , Hong Yubiao , Zheng Yu , Xue Mingqiang . Bis(β-diketiminato) Lanthanide(Ⅱ) Complexes-Catalyzed Hydro-phosphonylation of Aldehydes/Ketones and Diethyl Phosphite[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2168 -2174 . DOI: 10.6023/cjoc201603004
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