Nitrilium ions - synthesis and applications

被引:49
作者
van Dijk, Tom [1 ]
Slootweg, J. Chris [1 ,3 ]
Lammertsma, Koop [1 ,2 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, De Boelelaan 1083, NL-1081 HV Amsterdam, Netherlands
[2] Univ Johannesburg, Dept Chem, Auckland Pk, ZA-2006 Johannesburg, South Africa
[3] Univ Amsterdam, Vant Hoff Inst Mol Sci, Sci Pk 904,POB 94157, NL-1090 GD Amsterdam, Netherlands
关键词
N-ARYLNITRILIUM SALTS; ISOCYANIDE-BASED MCR; TRIFLUOROMETHANESULFONATE SALTS; X-RAY; PHOTOCHEMICAL GENERATION; MULTICOMPONENT REACTIONS; CATALYZED DECOMPOSITION; DIAZOCARBONYL COMPOUNDS; BECKMANN REARRANGEMENT; 3-COMPONENT SYNTHESIS;
D O I
10.1039/c7ob02533e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrilium ions have been well-established in organic chemistry for many decades, but recent developments show them to be far more versatile than hitherto recognized. They are known as stable salts, can be generated in situ, or are present as transient intermediates. We provide a succinct, but comprehensive review on the synthesis, stability, and reactivity of nitrilium ions as synthons for imines, their use in the synthesis of a large spectrum of heterocycles, and their reactions with transition metal complexes. By offering this overview, we aim for a renewed focus on readily accessible and simple to use nitrilium ions as valuable reagents for the synthesis of organic compounds.
引用
收藏
页码:10134 / 10144
页数:11
相关论文
共 142 条
[81]  
Kanemasa S., 2004, SCI SYNTH, V19, P53
[82]   Stereoselectivity of Additions to N-Methyl Acetonitrilium Fluorosulfonate [J].
Keese, Reinhart ;
Berdat, Francois ;
Macchi, Piero .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (05) :1965-1970
[83]  
KLAGES F, 1955, LIEBIGS ANN CHEM, V594, P21
[84]   Expedient entry into 1,4-dihydroquinoxalines and Quinoxalines via a novel variant of isocyanide-based MCR [J].
Krasavin, Mikhail ;
Parchinsky, Vladislav .
SYNLETT, 2008, (05) :645-648
[85]  
Krimen L.I., 1969, ORGANIC REACTIONS NE, V17, P213, DOI DOI 10.1002/0471264180.0R017.03
[86]   TMSCI-promoted isocyanide-based MCR of ethylenediamines: an efficient assembling of 2-aminopyrazine core [J].
Kysil, Volodymyr ;
Tkachenko, Sergey ;
Khvat, Alexander ;
Williams, Caroline ;
Tsirulnikov, Sergev ;
Churakova, Marina ;
Ivachtchenko, Alexandre .
TETRAHEDRON LETTERS, 2007, 48 (36) :6239-6244
[87]   Synthesis of Substituted Pyridines from Cascade [1+5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction [J].
Lei, Chuan-Hu ;
Wang, De-Xian ;
Zhao, Liang ;
Zhu, Jieping ;
Wang, Mei-Xiang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4708-4711
[88]   STUDIES ON THE MECHANISM OF THE VONBRAUN REACTION [J].
LEONARD, NJ ;
NOMMENSEN, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2808-2813
[89]   Synthesis and characterization of volatile liquid cobalt amidinates [J].
Li, Zhengwen ;
Lee, Don Kuen ;
Coulter, Michael ;
Rodriguez, Leonard N. J. ;
Gordon, Roy G. .
DALTON TRANSACTIONS, 2008, (19) :2592-2597
[90]   ACID-CATALYZED SOLVOLYSIS OF ISONITRILES .1. [J].
LIM, YY ;
STEIN, AR .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (14) :2455-&