Zinc-Catalyzed Organic Synthesis: C-C, C-N, C-O Bond Formation Reactions

被引:156
作者
Wu, Xiao-Feng [1 ,2 ]
Neumann, Helfried [2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse EV, D-18059 Rostock, Germany
关键词
C-C; C-N; C-O bond formation; green chemistry; homogenous catalyst; organic synthesis; zinc catalysts; FRIEDEL-CRAFTS ALKYLATION; MANNICH-TYPE REACTION; ONE-POT SYNTHESIS; HIGHLY STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC ALDOL REACTIONS; CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE REFORMATSKY REACTION; NITROALDOL HENRY REACTION; MEDIATED CHAIN EXTENSION; AMINO CARBONYL-COMPOUNDS;
D O I
10.1002/adsc.201200547
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Zinc is the 24th most abundant element in the Earths crust. Since the discovery of pure zinc metal in the 18th century, the main application of zinc metal is as materials. Because zinc salts are abundant, cheap, non-toxic, and exhibit environmentally benign properties, organic chemists have been interested in using zinc salts as catalysts in organic synthesis during the last three decades. Within this review, we have summarized the progress on applications of zinc salts in organic reactions. Our the target is to emphasize the special properties of zinc catalysts, and further promote the interest of organic chemists.
引用
收藏
页码:3141 / 3160
页数:20
相关论文
共 364 条
[1]   Dimethylzinc-Initiated Radical Reactions [J].
Akindele, Tito ;
Yamada, Ken-Ichi ;
Tomioka, Kiyoshi .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :345-355
[2]  
Alex K., 2008, Angew. Chem, V120, P2337
[3]   First synthesis of 4,5-dihydro-3(2H)-pyridazinones via Zn-mediated hydrohydrazination [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
TETRAHEDRON LETTERS, 2008, 49 (31) :4607-4609
[4]   General zinc-catalyzed intermolecular hydroamination of terminal alkynes [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
CHEMSUSCHEM, 2008, 1 (04) :333-338
[5]   Zinc-catalyzed synthesis of pyrazolines and pyrazoles via hydrohydrazination [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
ORGANIC LETTERS, 2008, 10 (12) :2377-2379
[6]   Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2304-2307
[7]   ZnCl2 as an efficient catalyst in the thiolysis of 1,2-epoxides by thiophenol in aqueous medium [J].
Amantini, D ;
Fringuelli, F ;
Pizzo, F ;
Tortoioli, S ;
Vaccaro, L .
SYNLETT, 2003, (15) :2292-2296
[8]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[9]   Direct electrophilic silylation of terminal alkynes [J].
Andreev, AA ;
Konshin, VV ;
Komarov, NV ;
Rubin, M ;
Brouwer, C ;
Gevorgyan, V .
ORGANIC LETTERS, 2004, 6 (03) :421-424
[10]   The role of Zn2+ in enhancing the rate and stereoselectivity of the aldol reactions catalyzed by the simple prolinamide model [J].
Andreu, Cecilia ;
Asensio, Gregorio .
TETRAHEDRON, 2011, 67 (37) :7050-7056