Room Temperature C-H Activation and Cross-Coupling of Aryl Ureas in Water

被引:168
作者
Nishikata, Takashi [1 ]
Abela, Alexander R. [1 ]
Lipshutz, Bruce H. [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
anilines; aryl urea; C-H activation; palladium; water; CATALYZED INTRAMOLECULAR ARYLATION; PROTON-ABSTRACTION MECHANISM; ANILIDE ORTHO-ARYLATION; DIRECT C-2 ARYLATION; PALLADIUM ACETATE; BOND ACTIVATION; INDOLES; FUNCTIONALIZATION; HETEROARENES; BORYLATION;
D O I
10.1002/anie.200905967
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Present) Just mix in water'n stir: Pd-catalyzed C-H activation/cross-couplings can be carried out at room temperature in water/surfactant mixtures. The combination of Pd-(OAc)2 and HBF 4 allowed for reactions of aryl ureas with aryl iodides under very mild conditions, using micellar catalysis (see scheme). This reaction is made possible by use of an in situ generated cationic palladium catalyst. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:781 / 784
页数:4
相关论文
共 48 条
[31]   Catalytic intermolecular direct arylation of perfluorobenzenes [J].
Lafrance, Marc ;
Rowley, Christopher N. ;
Woo, Tom K. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) :8754-8756
[32]  
LANE BS, 2008, J AM CHEM SOC, V130, P8050
[33]   Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles [J].
Lebrasseur, Nathalie ;
Larrosa, Igor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) :2926-2927
[34]   Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].
Li, Chao-Jun .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344
[35]  
Lipshutz BH, 2008, ALDRICHIM ACTA, V41, P59
[36]   Transition metal-catalyzed hydroarylation of alkynes [J].
Nevado, C ;
Echavarren, AM .
SYNTHESIS-STUTTGART, 2005, (02) :167-182
[37]   Allylic Ethers as Educts for Suzuki-Miyaura Couplings in Water at Room Temperature [J].
Nishikata, Takashi ;
Lipshutz, Bruce H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12103-+
[38]   Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline [J].
Ohnmacht, Stephan A. ;
Mamone, Patrizia ;
Culshaw, Andrew J. ;
Greaney, Michael F. .
CHEMICAL COMMUNICATIONS, 2008, (10) :1241-1243
[39]   Detailed Study of C-O and C-C Bond-Forming Reductive Elimination from Stable C2N2O2-Ligated Palladium(IV) Complexes [J].
Racowski, Joy M. ;
Dick, Allison R. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10974-10983
[40]   Steric Modulation of Chiral Biaryl Diamines via Pd-Catalyzed Directed C-H Arylation [J].
Scarborough, Christopher C. ;
McDonald, Richard I. ;
Hartmann, Caroline ;
Sazama, Graham T. ;
Bergant, Ana ;
Stahl, Shannon S. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2613-2615