Unravelling the labyrinth of palladium-catalysed reactions involving isocyanides

被引:299
作者
Lang, Stuart [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland
关键词
PD-C BOND; 3-COMPONENT REACTION; ARYL HALIDES; INSERTION; REACTIVITY; ISOTHIOCYANATES; COMPLEXES; AMIDINES; BROMOALKYNES; HETEROCYCLES;
D O I
10.1039/c3cs60022j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isocyanides possess a rich history in the world of synthetic chemistry. Recently the scope of this already versatile class of reagent has been expanded into its use in palladium-catalysed cascade sequences. The scope of this type of reaction is explored in depth and this tutorial review focuses on its various applications in chemical synthesis, and the wide range of systems that can be efficiently prepared using this strategy are documented.
引用
收藏
页码:4867 / 4880
页数:14
相关论文
共 53 条
[1]   Mechanistic Exploration of the Palladium-catalyzed Process for the Synthesis of Benzoxazoles and Benzothiazoles [J].
Bochatay, Valentin N. ;
Boissarie, Patrick J. ;
Murphy, John A. ;
Suckling, Colin J. ;
Lang, Stuart .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04) :1471-1477
[2]   A Powerful Palladium-Catalyzed Multicomponent Process for the Preparation of Oxazolines and Benzoxazoles [J].
Boissarie, Patrick J. ;
Hamilton, Zoe E. ;
Lang, Stuart ;
Murphy, John A. ;
Suckling, Colin J. .
ORGANIC LETTERS, 2011, 13 (23) :6256-6259
[3]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[4]   Migratory Insertion of Allyl Groups across the Pd-C Bond in Palladium(II) Isocyanide Complexes. The Fundamental Interplay between Temperature and Allyl Hapticity [J].
Canovese, Luciano ;
Visentin, Fabiano ;
Santo, Claudio ;
Levi, Carlo .
ORGANOMETALLICS, 2009, 28 (23) :6762-6770
[5]   Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones:: Synthesis of mappicines, camptothecins, and homocamptothecins [J].
Curran, DP ;
Du, W .
ORGANIC LETTERS, 2002, 4 (19) :3215-3218
[6]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[7]  
2-U
[8]   Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade [J].
Eckert, Heiner .
MOLECULES, 2012, 17 (01) :1074-1102
[9]   Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion [J].
Fei, Xiang-Dong ;
Ge, Zhi-Yuan ;
Tang, Ting ;
Zhu, Yong-Ming ;
Ji, Shun-Jun .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :10321-10328
[10]   Sequential Insertion of Alkynes and CO or Isocyanides into the Pd-C Bond of Cyclopalladated Phenylacetamides. Synthesis of Eight-Membered Palladacycles, Benzo[d]azocine-2,4(1H,3H)-diones, and Highly Functionalized Acrylonitrile and Acrylamide Derivatives [J].
Frutos-Pedreno, Roberto ;
Gonzalez-Herrero, Pablo ;
Vicente, Jose ;
Jones, Peter G. .
ORGANOMETALLICS, 2012, 31 (08) :3361-3372