A versatile and efficient ligand for copper-catalyzed formation of C-N, C-o, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester

被引:373
作者
Rao, HH
Jin, Y
Fu, H [1 ]
Jiang, YY
Zhao, YF
机构
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[2] Tsing Hua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China
关键词
arylation; copper; cross-coupling; homogeneous catalysis; N; O ligands;
D O I
10.1002/chem.200501473
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new and readily available bidentate ligand, namely, pyrrolidine-2-phosphonic acid phenyl monoester (PPAPM), has been developed for the coppercatalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the Cul/ PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
引用
收藏
页码:3636 / 3646
页数:11
相关论文
共 111 条
[61]  
LEI HY, 1992, SYNTHESIS-STUTTGART, P1255
[62]  
Ley S. V., 2003, ANGEW CHEM, V115, P5558, DOI [DOI 10.1002/ange.200300594, DOI 10.1002/ANIE.200300594]
[63]   Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].
Ley, SV ;
Thomas, AW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449
[64]   CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine [J].
Ma, DW ;
Liu, F .
CHEMICAL COMMUNICATIONS, 2004, (17) :1934-1935
[65]   Mild method for Ullmann coupling reaction of amines and aryl halides [J].
Ma, DW ;
Cai, Q ;
Zhang, H .
ORGANIC LETTERS, 2003, 5 (14) :2453-2455
[66]   N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides [J].
Ma, DW ;
Cai, Q .
ORGANIC LETTERS, 2003, 5 (21) :3799-3802
[67]   Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids.: Synthesis of benzolactam-V8 [J].
Ma, DW ;
Zhang, YD ;
Yao, JC ;
Wu, SH ;
Tao, FG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) :12459-12467
[68]   CuI-catalyzed coupling reaction of β-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction.: Facile synthesis of SB-214857 [J].
Ma, DW ;
Xia, CF .
ORGANIC LETTERS, 2001, 3 (16) :2583-2586
[69]   L-Proline promoted Ullmann-type coupling reactions of aryl iodides with indoles, pyrroles, imidazoles or pyrazoles [J].
Ma, DW ;
Cai, Q .
SYNLETT, 2004, (01) :128-130
[70]   Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers [J].
Mann, G ;
Incarvito, C ;
Rheingold, AL ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3224-3225