Mild Pd/Cu-Catalyzed Sila- Sonogashira Coupling of (Hetero)aryl Bromides with (Hetero)arylethynylsilanes under PTC Conditions

被引:28
作者
Bellina, Fabio [1 ]
Lessi, Marco [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
Sonogashira reaction; palladium; alkynylsilanes; diarylethynes; copper; phase-transfer catalysis; COPPER-FREE; ARYL IODIDES; AMBIENT CONDITIONS; ROOM-TEMPERATURE; TERMINAL ALKYNES; IONIC LIQUIDS; HECK REACTION; IN-SITU; ALKYNYLSILANES; WATER;
D O I
10.1055/s-0031-1290601
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium/copper cocatalyzed sila-Sonogashira reaction of (hetero)arylethynysilanes with (hetero) aryl bromides in toluene and water at 40 degrees C under PTC conditions gave the required di(hetero)arylethynes in moderate to high yields. Activated, deactivated and ortho-substituted (hetero) aryl bromides are well tolerated. This protocol also allowed the preparation of symmetrical diarylethynes by double arylation of 1,2-bis(trimethylsilyl)ethyne.
引用
收藏
页码:773 / 777
页数:5
相关论文
共 72 条
[1]   Oxime palladacycles revisited:: Stone-stable complexes nonetheless very active catalysts [J].
Alacid, Emilio ;
Alonso, Diego A. ;
Botella, Luis ;
Najera, Carmen ;
Pacheco, M. Carmen .
CHEMICAL RECORD, 2006, 6 (03) :117-132
[2]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[3]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[4]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[5]   Copper- and phosphine-free Sonogashira coupling reactions of aryl iodides catalyzed by an N,N-bis(naphthylideneimino)diethylenetriamine-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions [J].
Bakherad, Mohammad ;
Amin, Amir H. ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Raeissi, Mersad .
TETRAHEDRON LETTERS, 2010, 51 (43) :5653-5656
[6]   Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].
Bunz, UHF .
CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644
[7]   Convenient copper- and solvent-free Sonogashira-type alkynylation of aryl iodides and bromides using Pd EnCat™ [J].
Carpita, Adriano ;
Ribecai, Arianna .
TETRAHEDRON LETTERS, 2009, 50 (02) :204-207
[8]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[9]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[10]   Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc [J].
Crisp, GT ;
Turner, PD ;
Stephens, KA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 570 (02) :219-224