Pd2(dba)3/P(i-BuNCH2CH2)3N-catalyzed Stille cross-coupling of aryl chlorides

被引:73
作者
Su, WP [1 ]
Urgaonkar, S [1 ]
Verkade, JG [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/ol0495927
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pd-2(dba)(3)/P(i-BuNCH2CH2)(3)N (1d) catalyst system is highly effective for the Stille cross-coupling of aryl chlorides with organotin compounds. This method represents only the second general method for the coupling of aryl chlorides. Other proazaphosphatranes possessing benzyl substituents also generate very active catalysts for Stille reactions. Noteworthy features of the method are: (a) commercial availability of ligand 1d, (b) the wide array of aryl chlorides that can be coupled, and (c) applicability to aryl, vinyl, and allyl tin reagents.
引用
收藏
页码:1421 / 1424
页数:4
相关论文
共 42 条
[1]   Highly active catalysts for the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ .
CHEMICAL COMMUNICATIONS, 2001, (17) :1540-1541
[2]   Phenyl backbone-derived P,O- and P,N-ligands for palladium/ligand-catalyzed aminations of aryl bromides, iodides, and chlorides.: Syntheses and structures of (P,O)n-palladium(II)aryl(Br) complexes [J].
Bei, XH ;
Uno, T ;
Norris, J ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
ORGANOMETALLICS, 1999, 18 (10) :1840-1853
[3]   Total synthesis of the rubrolone aglycon [J].
Boger, DL ;
Ichikawa, S ;
Jiang, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) :12169-12173
[4]   Palladium-arene interactions in catalytic intermediates:: An experimental and theoretical investigation of the soft rearrangement between η1 and η2 coordination modes [J].
Catellani, M ;
Mealli, C ;
Motti, E ;
Paoli, P ;
Perez-Carreño, E ;
Pregosin, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4336-4346
[5]   Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes [J].
Choudary, BM ;
Madhi, S ;
Chowdari, NS ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14127-14136
[6]  
Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[7]   Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates [J].
Grasa, GA ;
Nolan, SP .
ORGANIC LETTERS, 2001, 3 (01) :119-122
[8]   Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370
[9]   Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].
Hartwig, JF ;
Kawatsura, M ;
Hauck, SI ;
Shaughnessy, KH ;
Alcazar-Roman, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580
[10]  
Herrmann WA, 1998, J ORGANOMET CHEM, V557, P93