Rhenium-Catalyzed Regioselective Alkylation of Phenols

被引：82

作者：

Kuninobu, Yoichiro ^{[1
]}

Matsuki, Takashi ^{[1
]}

Takai, Kazuhiko ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Chem & Biochem, Kita Ku, Okayama 7008530, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 29期

关键词：

C-H BOND; LIQUID-PHASE ALKYLATION; TERMINAL ACETYLENES; ANTI-MARKOVNIKOV; COMPLEXES; INSERTION; ACTIVATION; ARENES; HYDROARYLATION; ANNULATION;

D O I：

10.1021/ja904360k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of phenol derivatives with terminal alkenes in the presence of a catalytic amount of a rhenium complex, Re-2(CO)(10), gave monoalkylated phenol derivatives in good to excellent yields. This reaction proceeds at the ortho- or para-position of phenols regioselectively.

引用

页码：9914 / +

页数：3

共 32 条

[1] The Friedel-Crafts syntheses [J].

Calloway, NO .

CHEMICAL REVIEWS, 1935, 17 (03) :327-392

[2] Halide-free ethylation of phenol by multifunctional catalysis using phosphinite ligands [J].

Carrion, M. Carmen ;

Cole-Hamilton, David J. .

CHEMICAL COMMUNICATIONS, 2006, (43) :4527-4529

[3] Highly efficient iodine-catalyzed hydroarylation of arenes with styrenes [J].

Chu, Cheng-Ming ;

Huang, Wan-Ju ;

Liu, Ju-Tsung ;

Yao, Ching-Fa .

TETRAHEDRON LETTERS, 2007, 48 (39) :6881-6885

[4] Addition of the ortho-C-H bonds of phenol across an olefin catalysed by a chiral iridium(I) diphosphine complex [J].

Dorta, R ;

Togni, A .

CHEMICAL COMMUNICATIONS, 2003, (06) :760-761

[5] Catalytic performance of Preyssler heteropolyacid, [NaP5W30O110]14- in liquid phase alkylation of phenol with 1-octene [J].

Hekmatshoar, Rahim ;

Heravi, Majid M. ;

Sadjadi, Sodeh ;

Oskooie, Hossein A. ;

Bamoharram, Faterneh F. .

CATALYSIS COMMUNICATIONS, 2008, 9 (05) :837-841

[6] ZIRCONIUM-CATALYZED COUPLING OF PROPENE AND ALPHA-PICOLINE [J].

JORDAN, RF ;

TAYLOR, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :778-779

[7] Methyltrioxorhenium and its applications in olefin oxidation, metathesis and aldehyde olefination [J].

Kühn, FE ;

Scherbaum, A ;

Herrmann, WA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4149-4164

[8] Rhenium-catalyzed insertion of terminal acetylenes into a C-H bond of active methylene compounds [J].

Kuninobu, Y ;

Kawata, A ;

Takai, K .

ORGANIC LETTERS, 2005, 7 (22) :4823-4825

[9] Rhenium-catalyzed formation of indene frameworks via C-H bond activation: [3+2] annulation of aromatic aldimines and acetylenes [J].

Kuninobu, Y ;

Kawata, A ;

Takai, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13498-13499

[10] Rhenium-catalyzed coupling of 2-propynyl alcohols and several nucleophiles via dehydration [J].

Kuninobu, Yoichiro ;

Ueda, Hirokazu ;

Takai, Kazuhiko .

CHEMISTRY LETTERS, 2008, 37 (08) :878-879

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