Gold-Catalyzed Oxidative Coupling Reactions with Aryltrimethylsilanes

被引:125
作者
Brenzovich, William E., Jr. [1 ]
Brazeau, Jean-Francois [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
BORONIC ACIDS; ORGANIC-COMPOUNDS; ARYL; FLUORINATION; ALTERNATIVES; DERIVATIVES; REACTIVITY; BROMIDES; COMPLEX; STILLE;
D O I
10.1021/ol102194c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
During continuing studies with a novel oxidative gold oxyarylation reaction, arylsilanes were found to be competent coupling partners, providing further evidence for an intramolecular electrophilic aromatic substitution mechanism. While providing yields complementary to those of the previously described boronic acid methods, the use of trimethylsilanes reduces the observation of homocoupling byproducts and allows for facile intramolecular coupling reactions.
引用
收藏
页码:4728 / 4731
页数:4
相关论文
共 45 条
[1]  
[Anonymous], 2004, METAL CATALYZED CROS
[2]  
[Anonymous], 2004, METAL CATALYZED CROS
[3]   Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].
Brenzovich, William E., Jr. ;
Benitez, Diego ;
Lackner, Aaron D. ;
Shunatona, Hunter P. ;
Tkatchouk, Ekaterina ;
Goddard, William A., III ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522
[4]  
CHAN TH, 1979, SYNTHESIS-STUTTGART, P761
[5]  
DAVID V, 2006, ANGEW CHEM INT EDIT, V45, P8188
[6]   Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods [J].
Denmark, Scott E. ;
Regen, Christopher S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1486-1499
[7]   Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions [J].
Denmark, Scott. E. ;
Baird, John D. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (19) :4954-4963
[8]   Palladium- (and nickel-) catalyzed vinylation of aryl halides [J].
Denmark, Scott E. ;
Butler, Christopher R. .
CHEMICAL COMMUNICATIONS, 2009, (01) :20-33
[9]   Fluoride-free cross-coupling of organosilanols [J].
Denmark, SE ;
Sweis, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6439-6440
[10]   Novel palladium-catalyzed atom-efficient cross-coupling reaction by means of hexaarylcyclotrisiloxane [J].
Endo, Mayuko ;
Sakurai, Tomoyuki ;
Ojima, Satoshi ;
Katayama, Takako ;
Unno, Masafumi ;
Matsumoto, Hideyuki ;
Kowase, Susumu ;
Sano, Hiroshi ;
Kosugi, Masanori ;
Fugami, Keigo .
SYNLETT, 2007, (05) :749-752