Progress and developments in the turbo Grignard reagent i-PrMgCl•LiCl: a ten-year journey

被引:137
作者
Bao, Robert Li-Yuan [1 ]
Zhao, Rong [1 ]
Shi, Lei [1 ]
机构
[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, Inst Organ Chem, Harbin 150080, Peoples R China
关键词
CROSS-COUPLING REACTIONS; BROMINE-MAGNESIUM EXCHANGE; DIELS-ALDER REACTIONS; POLYFUNCTIONAL ARYL; REGIOSELECTIVE FUNCTIONALIZATION; STEREOSELECTIVE PREPARATION; ALKENYLMAGNESIUM REAGENTS; PARA-DIFUNCTIONALIZATION; PHOSPHOROTHIOATE ESTERS; FULL FUNCTIONALIZATION;
D O I
10.1039/c4cc10194d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the past decade, the effectiveness of i-PrMgCl center dot LiCl has been constantly highlighted by a number of research groups. Its enhanced nucleophilicity brings prosperity to highly functionalized Grignard reagents, other useful bimetallic (alkali-metal) agents and nucleophilic alkylation products under mild reaction conditions. In this feature article, a comprehensive, systematical and in-depth overview of i-PrMgCl center dot LiCl is provided in a multidisciplinary idea. It involves the structural and kinetic perspectives of i-PrMgCl center dot LiCl as well as its unique reactivity and selectivity, with knowledge of the former helping to rationalize trends of the later.
引用
收藏
页码:6884 / 6900
页数:17
相关论文
共 193 条
[61]   Calix[4]arenes with intramolecularly bridged meta positions prepared via Pd-catalysed double C-H activation [J].
Holub, Jan ;
Eigner, Vaclav ;
Vrzal, Lukas ;
Dvorakova, Hana ;
Lhotak, Pavel .
CHEMICAL COMMUNICATIONS, 2013, 49 (27) :2798-2800
[62]   Grignard Metathesis Chain-Growth Polymerization for Polyfluorenes [J].
Huang, Li ;
Wu, Shupeng ;
Qu, Yao ;
Geng, Yanhou ;
Wang, Fosong .
MACROMOLECULES, 2008, 41 (22) :8944-8947
[63]   Palladium-Catalyzed Cross-Coupling of Aziridinylmetal Species, Generated by Sulfinyl-Magnesium Exchange, with Aryl Bromides: Reaction Optimization, Scope, and Kinetic Investigations [J].
Hughes, Matthew ;
Boultwood, Tom ;
Zeppetelli, Gianfranco ;
Bull, James A. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03) :844-854
[64]   KINETIC EVIDENCE FOR REACTIVE INTERMEDIATES [J].
HUISGEN, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (10) :751-&
[65]   Preparation and Regioselective Diels-Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates [J].
Ikawa, Takashi ;
Takagi, Akira ;
Kurita, Yurio ;
Saito, Kozumo ;
Azechi, Kenji ;
Egi, Masahiro ;
Kakiguchi, Keisuke ;
Kita, Yasuyuki ;
Akai, Shuji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5563-5566
[66]   Preparation and reactions of heteroaryl organomagnesium compounds [J].
Ila, H ;
Baron, O ;
Wagner, AJ ;
Knochel, P .
CHEMISTRY LETTERS, 2006, 35 (01) :2-7
[67]   Functionalized magnesium organometallics as versatile intermediates for the synthesis of polyfunctional heterocycles [J].
Ila, H ;
Baron, O ;
Wagner, AJ ;
Knochel, P .
CHEMICAL COMMUNICATIONS, 2006, (06) :583-593
[68]   Rigid P-Chiral Phosphine Ligands with tert-Butylmethylphosphino Groups for Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes [J].
Imamoto, Tsuneo ;
Tamura, Ken ;
Zhang, Zhenfeng ;
Horiuchi, Yumi ;
Sugiya, Masashi ;
Yoshida, Kazuhiro ;
Yanagisawa, Akira ;
Gridnev, Ilya D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1754-1769
[69]   Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles [J].
Ishii, Genki ;
Harigae, Ryo ;
Moriyama, Katsuhiko ;
Togo, Hideo .
TETRAHEDRON, 2013, 69 (05) :1462-1469
[70]   Catalytic Enantioselective Arylation of Aldehydes by Using Functionalized Grignard Reagents Generated from Aryl Bromides [J].
Itakura, Daisuke ;
Harada, Toshiro .
SYNLETT, 2011, (19) :2875-2879