Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature

被引:164
作者
Zhu, W
Ma, DW
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
关键词
D O I
10.1021/ol052633u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling reaction of pinacolborane with aryl iodides under the catalysis of 10 mol % Cul and the action of sodium hydride in THF works at room temperature to provide corresponding arylboronates in good yields. Aryl bromides give poor conversion under these reaction conditions.
引用
收藏
页码:261 / 263
页数:3
相关论文
共 25 条
[1]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[2]   Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions [J].
Cai, Q ;
Zhu, W ;
Zhang, H ;
Zhang, YD ;
Ma, DW .
SYNTHESIS-STUTTGART, 2005, (03) :496-499
[3]   Intramolecular O-arylation of phenols with phenylboronic acids: Application to the synthesis of macrocyclic metalloproteinase inhibitors [J].
Decicco, CP ;
Song, Y ;
Evans, DA .
ORGANIC LETTERS, 2001, 3 (07) :1029-1032
[4]   Total synthesis of anti-HIV agent chloropeptin I [J].
Deng, HB ;
Jung, JK ;
Liu, T ;
Kuntz, KW ;
Snapper, ML ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9032-9034
[5]   A NEW SYNTHESIS OF ARYL FLUORIDES - THE REACTION OF CESIUM FLUOROXYSULFATE WITH ARYLBORONIC ACIDS AND DERIVATIVES [J].
DIORAZIO, LJ ;
WIDDOWSON, DA ;
CLOUGH, JM .
TETRAHEDRON, 1992, 48 (37) :8073-8088
[6]   A σ4, λ5-phosphinine palladium complex:: a new type of phosphorus ligand and catalyst.: Application to the Pd-catalyzed formation of arylboronic esters [J].
Doux, M ;
Mézailles, N ;
Melaimi, M ;
Ricard, L ;
Le Floch, P .
CHEMICAL COMMUNICATIONS, 2002, (15) :1566-1567
[7]   Enantioselective synthesis of 4-substituted phenylalanines by cross-coupling reactions [J].
Firooznia, F ;
Gude, C ;
Chan, K ;
Marcopulos, N ;
Satoh, Y .
TETRAHEDRON LETTERS, 1999, 40 (02) :213-216
[8]   Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system [J].
Fürstner, A ;
Seidel, G .
ORGANIC LETTERS, 2002, 4 (04) :541-543
[9]   Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes [J].
Ishiyama, T ;
Ishida, K ;
Miyaura, N .
TETRAHEDRON, 2001, 57 (49) :9813-9816
[10]   PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].
ISHIYAMA, T ;
MURATA, M ;
MIYAURA, N .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510