Reductive Umpolung Reactions with Low-Valent Titanium Catalysts

被引：50
作者：
Streuff, Jan [1 ]
机构：
[1] Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany
来源：
CHEMICAL RECORD | 2014年 / 14卷 / 06期
关键词：
homogeneous catalysis; radical reactions; reduction; titanium; umpolung; QUATERNARY STEREOGENIC CENTERS; PINACOL COUPLING REACTION; CONJUGATE ADDITION; ELECTRON-TRANSFER; RADICAL CYCLIZATION; ARYL HALIDES; ACTIVATED ALKENES; ALKYL-HALIDES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC 1,4-ADDITION;
D O I：
10.1002/tcr.201402058
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The coupling of similarly polarized carbon fragments can be achieved by a reductive umpolung strategy. This gives access to compounds with functional groups in even bond distances, which are difficult to synthesize by other means. Low-valent titanium catalysts enable such couplings under mild conditions. This account covers the recent progress on this topic with a focus on the development of cross-selective coupling reactions and stereoselective examples.
引用
收藏
页码：1100 / 1113
页数：14
相关论文
共 181 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]   CoBr2(bpy):: An efficient catalyst for the direct conjugate addition of aryl halides or triflates onto activated olefins [J].
Amatore, Muriel ;
Gosmini, Corinne ;
Perichon, Jacques .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6130-6134
[3]   THE REACTION OF ARYL IODIDES WITH HINDERED ALPHA,BETA,GAMMA,DELTA-DIENONES IN THE PRESENCE OF THE [PD(OAC)2(PPH3)2]-TRIALKYLAMMONIUM FORMATE REAGENT [J].
ARCADI, A ;
MARINELLI, F ;
CACCHI, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 312 (02) :C27-C32
[4]   Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium Schiff base complexes [J].
Bandini, M ;
Cozzi, PG ;
Morganti, S ;
Umani-Ronchi, A .
TETRAHEDRON LETTERS, 1999, 40 (10) :1997-2000
[5]   Titanocene-catalysed, selective reduction of ketones in aqueous media.: A safe, mild, inexpensive procedure for the synthesis of secondary alcohols via radical chemistry [J].
Barrero, AF ;
Rosales, A ;
Cuerva, JM ;
Gansäuer, A ;
Oltra, JE .
TETRAHEDRON LETTERS, 2003, 44 (05) :1079-1082
[6]   Couplings of benzylic halides mediated by titanocene chloride:: Synthesis of bibenzyl derivatives [J].
Barrero, Alejandro F. ;
Herrador, M. Mar ;
Quilez del Moral, Jose F. ;
Arteaga, Pilar ;
Akssira, Mohammed ;
El Hanbali, Fadwa ;
Arteaga, Jesus F. ;
Dieguez, Horacio R. ;
Sanchez, Elena M. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :2251-2254
[7]   Unusual Nitrile-Nitrile and Nitrile-Alkyne Coupling of Fc-C≡N and Fc-C≡C-C≡N [J].
Becker, Lisanne ;
Strehler, Frank ;
Korb, Marcus ;
Arndt, Perdita ;
Spannenberg, Anke ;
Baumann, Wolfgang ;
Lang, Heinrich ;
Rosenthal, Uwe .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (11) :3061-3068
[8]   Nitrile-Nitrile C-C Coupling at Group 4 Metallocenes to Form 1-Metalla-2,5-diaza-cyclopenta-2,4-dienes: Synthesis and Reactivity [J].
Becker, Lisanne ;
Arndt, Perdita ;
Jiao, Haijun ;
Spannenberg, Anke ;
Rosenthal, Uwe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) :11396-11400
[9]   Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles [J].
Beemelmanns, Christine ;
Reissig, Hans-Ulrich .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2199-2210
[10]   Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes [J].
Bensari, A ;
Renaud, JL ;
Riant, O .
ORGANIC LETTERS, 2001, 3 (24) :3863-3865
12345678910