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

[11] Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane [J].

Kimura, M ;

Futamata, M ;

Mukai, R ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4592-4593

[12] Alkylation of arenes with benzylic and propargylic alcohols -: Classical versus fancy catalysts [J].

Liu, JH ;

Muth, E ;

Flörke, U ;

Henkel, G ;

Merz, K ;

Sauvageau, J ;

Schwake, E ;

Dyker, G .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (4-5) :456-462

[13] Calix[n]arene sulfonic acids bearing pendant aliphatic chains as recyclable surfactant-type Bronsted acid catalysts for allylic alkylation with allyl alcohols in water [J].

Liu, Yu-Liang ;

Liu, Li ;

Wang, Yi-Lin ;

Han, Yu-Chun ;

Wang, Dong ;

Chen, Yong-Jun .

GREEN CHEMISTRY, 2008, 10 (06) :635-640

[14] Molybdenum(IV) complexes as efficient, Lewis acidic catalysts for allylic substitution. Formation of C-C and C-N bonds [J].

Malkov, AV ;

Spoor, P ;

Vinader, V ;

Kocovsky, P .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5308-5311

[15] Remarkable effect of N-substituent on enantioselective ruthenium-catalyzed propargylation of indoles with propargylic alcohols [J].

Matsuzawa, Hiroshi ;

Kanao, Keiichiro ;

Miyake, Yoshihiro ;

Nishibayashi, Yoshiaki .

ORGANIC LETTERS, 2007, 9 (26) :5561-5564

[16] Ruthenium-catalyzed enantioselective prolpargylation of aromatic compounds with propargylic alcohols via allenylidene intermediates [J].

Matsuzawa, Hiroshi ;

Miyake, Yoshihiro ;

Nishibayashi, Yoshiaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6488-6491

[17] Transition-metal-catalyzed benzylation of arenes and heteroarenes [J].

Mertins, K ;

Iovel, I ;

Kischel, J ;

Zapf, A ;

Beller, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :238-242

[18] Gold-catallyzed benzylation of arenes and heteroarenes [J].

Mertins, K ;

Lovel, I ;

Kischel, J ;

Zapf, A ;

Beller, M .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :691-695

[19] Chiral α-branched benzylic carbocations:: Diastereoselective intermolecular reactions with arene nucleophiles and NMR spectroscopic studies [J].

Muehlthau, Friedrich ;

Stadler, Daniel ;

Goeppert, Alain ;

Olah, George A. ;

Prakash, G. K. Surya ;

Bach, Thorsten .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9668-9675

[20] Hg(OTf)2-catalyzed arylene cyclization [J].

Namba, Kosuke ;

Yamamoto, Hirofumi ;

Sasaki, Ikuo ;

Mori, Kumiko ;

Imagawa, Hiroshi ;

Nishizawa, Mugio .

ORGANIC LETTERS, 2008, 10 (09) :1767-1770

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