Palladium-catalyzed suzuki-miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates

被引:96
作者
Zhang, Liang
Meng, Tianhao
Wu, Jie
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo7019064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[Graphics] Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl tosylates with potassium aryl trifluoroborate in the presence of bulky and electron-rich phosphine ligand is described. In addition, a useful chemoselective coupling of an aryl chloride in the presence of a tosyloxy group was demonstrated.
引用
收藏
页码:9346 / 9349
页数:4
相关论文
共 61 条
[1]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[2]   Microwave-promoted Suzuki coupling reactions with organotrifluoroborates in water using ultra-low catalyst loadings [J].
Arvela, RK ;
Leadbeater, NE ;
Mack, TL ;
Kormos, CM .
TETRAHEDRON LETTERS, 2006, 47 (02) :217-220
[3]   PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES [J].
BADONE, D ;
CECCHI, R ;
GUZZI, U .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6321-6323
[4]   Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides [J].
Barder, TE ;
Buchwald, SL .
ORGANIC LETTERS, 2004, 6 (16) :2649-2652
[5]   Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters [J].
Baxter, JM ;
Steinhuebel, D ;
Palucki, M ;
Davies, IW .
ORGANIC LETTERS, 2005, 7 (02) :215-218
[6]   Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts [J].
Cella, R ;
Cunha, RLOR ;
Reis, AES ;
Pimenta, DC ;
Klitzke, CF ;
Stefani, HA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :244-250
[7]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[8]   Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].
Darses, S ;
Genet, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327
[9]   Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides [J].
Fang, GH ;
Yan, ZJ ;
Deng, MZ .
ORGANIC LETTERS, 2004, 6 (03) :357-360
[10]   First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction [J].
Fu, XY ;
Zhang, SY ;
Yin, JG ;
McAllister, TL ;
Jiang, SA ;
Tann, CH ;
Thiruvengadam, TK ;
Zhang, FC .
TETRAHEDRON LETTERS, 2002, 43 (04) :573-576