Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids

被引:132
作者
McLaughlin, M [1 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1021/ol0517271
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or potassium carbonate as the base and toluene as the solvent at 90 degrees C. Using the developed conditions, a series of structurally diverse diarylmethanes were prepared.
引用
收藏
页码:4875 / 4878
页数:4
相关论文
共 25 条
[11]   Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis [J].
Kotha, S ;
Lahiri, K ;
Kashinath, D .
TETRAHEDRON, 2002, 58 (48) :9633-9695
[12]   Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids [J].
Kuwano, R ;
Yokogi, M .
ORGANIC LETTERS, 2005, 7 (05) :945-947
[13]   Selective double Suzuki cross-coupling reactions.: Synthesis of unsymmetrical diaryl (or heteroaryl) methanes [J].
Langle, S ;
Abarbri, M ;
Duchêne, A .
TETRAHEDRON LETTERS, 2003, 44 (52) :9255-9258
[14]   Palladium-catalysed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles [J].
Lepifre, F ;
Buon, C ;
Rabot, R ;
Bouyssou, P ;
Coudert, G .
TETRAHEDRON LETTERS, 1999, 40 (35) :6373-6376
[15]  
Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[16]  
2-U
[17]   Rational design and synthesis of novel dimeric diketoacid-containing inhibitors of HIV-1 integrase: Implication for binding to two metal ions on the active site of integrase [J].
Long, YQ ;
Jiang, XH ;
Dayam, R ;
Sanchez, T ;
Shoemaker, R ;
Sei, S ;
Neamati, N .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (10) :2561-2573
[18]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[19]  
Miyaura N, 2002, TOP CURR CHEM, V219, P11
[20]   Nickel-catalyzed cross-couplings of cyclohexenyl phosphate and arylboronic acids [J].
Nan, Y ;
Yang, Z .
TETRAHEDRON LETTERS, 1999, 40 (17) :3321-3324