Palladium(II)-Catalyzed coupling of p-xylene via regioselective C-H activation in TFA

被引：84

作者：

Rong, Ying ^{[1
]}

Li, Ruoshi ^{[1
]}

Lu, Wenjun ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Dept Chem, Shanghai 200240, Peoples R China

来源：

ORGANOMETALLICS | 2007年 / 26卷 / 18期

关键词：

D O I：

10.1021/om700418h

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A homocoupling of p-xylene to afford biaryl- or diarylmethane as a major product has been carried out in a catalytic system of Pd(OAc)(2)/CF3CO2H (TFA)/K2S2O8. In this coupling reaction, the aryl and benzylic C-H bonds of p-xylene can be selectively activated just by tuning the concentration of TFA.

引用

页码：4376 / 4378

页数：3

共 18 条

[1] Base-promoted selective activation of benzylic carbon-hydrogen bonds of toluenes by rhodium(III) porphyrins [J].

Chan, Kin Shing ;

Chiu, Peng Fai ;

Choi, Kwong Shing .

ORGANOMETALLICS, 2007, 26 (05) :1117-1119

[2] Mechanism of C-H bond activation of alkyl-substituted benzenes by cationic platinum(II) complexes [J].

Driver, TG ;

Day, MW ;

Labinger, JA ;

Bercaw, JE .

ORGANOMETALLICS, 2005, 24 (15) :3644-3654

[3] C-H bond activation by dicationic platinum(II) complexes [J].

Driver, Tom G. ;

Williams, Travis J. ;

Labinger, Jay A. ;

Bercaw, John E. .

ORGANOMETALLICS, 2007, 26 (02) :294-301

[4] Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation [J].

García-Cuadrado, D ;

Braga, AAC ;

Maseras, F ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1066-1067

[5] Kinetic and thermodynamic preferences in Aryl vs benzylic C-H bond activation with cationic Pt(II) complexes [J].

Heyduk, AF ;

Driver, TG ;

Labinger, JA ;

Bercaw, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15034-15035

[6] Highly regioselective catalytic oxidative coupling reactions: Synthetic and mechanistic investigations [J].

Hull, Kami L. ;

Lanni, Erica L. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14047-14049

[7] Unexpected selectivities in C-H activations of toluene and p-xylene at cationic platinum(II) diimine complexes.: New mechanistic insight into product-determining factors [J].

Johansson, L ;

Ryan, OB ;

Romming, C ;

Tilset, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6579-6590

[8] Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage [J].

Kakiuchi, F ;

Tsuchiya, K ;

Matsumoto, M ;

Mizushima, B ;

Chatani, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) :12792-12793

[9] MECHANISM OF OXIDATION OF METHYLBENZENES BY PALLADIUM(II) IN TRIFLUOROACETIC-ACID - ONE-ELECTRON TRANSFER AND ELECTROPHILIC SUBSTITUTION [J].

KOZHEVNIKOV, IV ;

KIM, VI ;

TALZI, EP ;

SIDELNIKOV, VN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1392-1394

[10] Understanding and exploiting C-H bond activation [J].

Labinger, JA ;

Bercaw, JE .

NATURE, 2002, 417 (6888) :507-514

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