CuI-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reactions using DABCO as ligand

被引:282
作者
Li, Jin-Heng [1 ]
Li, Ji-Lan [1 ]
Wang, De-Ping [1 ]
Pi, Shao-Feng [1 ]
Xie, Ye-Xiang [1 ]
Zhang, Man-Bo [1 ]
Hu, Xi-Chao [1 ]
机构
[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Coll Chem & Chem Engn, Changsha 410081, Peoples R China
关键词
D O I
10.1021/jo0623742
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of TBAB, CuI-catalyzed Suzuki-Miyaura cross-coupling of vinyl halides and aryl halides with arylboronic acids was conducted smoothly to afford the corresponding diarylethenes and polyaryls in moderate to good yields using DABCO (1,4-diazabicyclo[2.2.2]octane) as the ligand. We also found that the inexpensive CuI/DABCO catalytic system was effective for Sonogashira cross-couplings of aryl halides and vinyl halides. A variety of aryl halides and vinyl halides including activated aryl chlorides underwent the coupling with terminal alkynes in moderate to excellent yields.
引用
收藏
页码:2053 / 2057
页数:5
相关论文
共 43 条
[11]   PEG-400 promoted Pd(OAc)2/DABCO-catalyzed cross-coupling reactions in aqueous media [J].
Li, JH ;
Hu, XC ;
Liang, Y ;
Xie, YX .
TETRAHEDRON, 2006, 62 (01) :31-38
[12]   Pd(OAc)2/DABCO as an inexpensive and efficient catalytic system for Hiyama cross-coupling reactions of aryl halides with aryltrimethoxysilanes [J].
Li, JH ;
Deng, CL ;
Liu, WJ ;
Xie, YX .
SYNTHESIS-STUTTGART, 2005, (18) :3039-3044
[13]   Pd(OAc)2/DABCO as a highly active catalytic system for the Heck reaction [J].
Li, JH ;
Wang, DP ;
Xie, YX .
SYNTHESIS-STUTTGART, 2005, (13) :2193-2197
[14]   Recyclable and reusable Pd(OAc)2/DABCO/PEG-400 system for Suzuki-Miyaura cross-coupling reaction [J].
Li, JH ;
Liu, WJ ;
Xie, YX .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5409-5412
[15]   CuI/Dabco as a highly active catalytic system for the Heck-type reaction [J].
Li, JH ;
Wang, DP ;
Xie, Y .
TETRAHEDRON LETTERS, 2005, 46 (30) :4941-4944
[16]   Efficient Stille cross-coupling reaction catalyzed by the Pd(OAc)2/Dabco catalytic system [J].
Li, JH ;
Liang, Y ;
Wang, DP ;
Liu, WJ ;
Xie, YX ;
Yin, DL .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2832-2834
[17]   Efficient and copper-free Pd(OAc)2/DABCO-catalyzed Sonogashira cross-coupling reaction [J].
Li, JH ;
Zhang, XD ;
Xie, YX .
SYNTHESIS-STUTTGART, 2005, (05) :804-808
[18]   Dabco as an inexpensive and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction [J].
Li, JH ;
Liu, WJ .
ORGANIC LETTERS, 2004, 6 (16) :2809-2811
[19]   Polymer-supported DABCO-palladium complex as a stable and reusable catalyst for room temperature Suzuki-Miyaura cross-couplings of aryl bromides [J].
Li, Jin-Heng ;
Hu, Xi-Chao ;
Me, Ye-Xiang .
TETRAHEDRON LETTERS, 2006, 47 (52) :9239-9243
[20]   Pd(OAc)2/DABCO-catalyzed Suzuki-Miyaura cross-coupling reaction in DMF [J].
Li, Jin-Heng ;
Zhu, Qi-Ming ;
Xie, Ye-Xiang .
TETRAHEDRON, 2006, 62 (47) :10888-10895