π-Activated alcohols: an emerging class of alkylating agents for catalytic Friedel-Crafts reactions

被引：244

作者：

Bandini, Marco ^{[1
]}

Tragni, Michele ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 08期

关键词：

NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ALCOHOLS; AROMATIC-COMPOUNDS; BENZYL ALCOHOLS; ALLYL ALCOHOLS; REGIOSELECTIVE ALLYLATION; INDOLES; EFFICIENT; ARENES; CARBOCATIONS;

D O I：

10.1039/b823217b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct functionalization of aromatic compounds, via Friedel-Crafts alkylation reactions with alcohols, is one of the cornerstones in organic chemistry. The present emerging area deals with the recent advances in the use of pi-activated alcohols in the catalytic and stereoselective construction of benzylic stereocenters.

引用

页码：1501 / 1507

页数：7

共 45 条

[1] Ligand-Free Silver(I)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Arenes with Allylic Alcohols [J].

Bandini, Marco ;

Eichholzer, Astrid ;

Kotrusz, Peter ;

Tragni, Michele ;

Troisi, Stefano ;

Umani-Ronchi, Achille .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) :319-324

[2] Cooperative Friedel-Crafts catalysis in heterobimetallic regime:: Alkylation of aromatics by π-activated alcohols [J].

Choudhury, J ;

Podder, S ;

Roy, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6162-6163

[3] Diastereoselective Friedel-Crafts alkylation of indoles with chiral (α-phenyl benzylic cations.: Asymmetric synthesis of anti-1,1,2-triarylalkanes [J].

Chung, John Y. L. ;

Mancheno, Danny ;

Dormer, Peter G. ;

Variankaval, Narayan ;

Ball, Richard G. ;

Tsou, Nancy N. .

ORGANIC LETTERS, 2008, 10 (14) :3037-3040

[4] Nucleophilic substitution of ferrocenyl alcohols "on water'' [J].

Cozzi, Pier Giorgio ;

Zoli, Luca .

GREEN CHEMISTRY, 2007, 9 (12) :1292-1295

[5] Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols [J].

Georgy, M ;

Boucard, V ;

Campagne, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14180-14181

[6] Gold (III)-catalyzed direct nucleophilic substitution of propargylic alcohols [J].

Georgy, Marie ;

Boucard, Valerie ;

Debleds, Olivier ;

Dal Zotto, Christophe ;

Campagne, Jean-Marc .

TETRAHEDRON, 2009, 65 (09) :1758-1766

[7] Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols [J].

Inada, Y ;

Yoshikawa, M ;

Milton, MD ;

Nishibayashi, Y ;

Uemura, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (04) :881-890

[8] An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates [J].

Iovel, I ;

Mertins, K ;

Kischel, J ;

Zapf, A ;

Beller, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3913-3917

[9] An FeCl3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols [J].

Jana, Umasish ;

Maiti, Sukhendu ;

Biswas, Srijit .

TETRAHEDRON LETTERS, 2007, 48 (40) :7160-7163

[10] Rhenium-catalyzed aromatic propargylation [J].

Kennedy-Smith, JJ ;

Young, LA ;

Toste, FD .

ORGANIC LETTERS, 2004, 6 (08) :1325-1327

← 1 2 3 4 5 →