Phosphorylation of C - H bonds of aromatic compounds using metals and metal complexes

被引:56
作者
Budnikova, Yu H. [1 ]
Sinyashin, O. G. [1 ]
机构
[1] Russian Acad Sci, Kazan Sci Ctr, AE Arbuzov Organ & Phys Chem Inst, Kazan 420088, Russia
基金
俄罗斯基础研究基金会;
关键词
CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED PHOSPHONATION; INTRAMOLECULAR RADICAL TRANSFER; FORMING REDUCTIVE ELIMINATION; REVERSE-TRANSCRIPTASE; DIALKYL PHOSPHITES; ARYLBORONIC ACIDS; DIRECT AMINATION; ARYL HALIDES; OXIDATIVE PHOSPHONYLATION;
D O I
10.1070/RCR4525
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Key achievements and current trends in the development of methods for phosphorylation of aromatic C - H bonds catalyzed by metal salts and complexes are considered. The most important and promising approaches of the last decade, including those concerning the synthesis and properties of arylphosphonates, are distinguished. Methods for the introduction of a phosphonate group into non-activated and functionally substituted aromatic compounds and heteroaromatic molecules and phosphorylation cyclization reactions involving acetylenes, 2-isocyanobiphenyls and alkynoates are analyzed. The possibilities of ligand-directed phosphorylation of compounds with aromatic C - H bonds and presumed mechanisms and intermediates in the C - P bond formation reactions are considered. The potential of this extensively developing research trend in organic and organoelement chemistry is highlighted.
引用
收藏
页码:917 / 951
页数:35
相关论文
共 266 条
[1]   New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense [J].
Abdel-Halim, OB ;
Morikawa, T ;
Ando, S ;
Matsuda, H ;
Yoshikawa, M .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07) :1119-1124
[2]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[3]   Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Pospech, Jola .
ORGANIC LETTERS, 2010, 12 (04) :724-726
[4]   Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends [J].
Albrecht, Martin .
CHEMICAL REVIEWS, 2010, 110 (02) :576-623
[5]   Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors [J].
Alexandre, Francois-Rene ;
Amador, Agnes ;
Bot, Stephanie ;
Caillet, Catherine ;
Convard, Thierry ;
Jakubik, Jocelyn ;
Musiu, Chiara ;
Poddesu, Barbara ;
Vargiu, Luana ;
Liuzzi, Michel ;
Roland, Arlene ;
Seifer, Maria ;
Standring, David ;
Storer, Richard ;
Dousson, Cyril B. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :392-395
[6]   A one step nickel(II)-catalysed synthesis of tris-{2-(2-benzothiazolyl)phenyl}phosphine from tris(hydroxymethyl)phosphine.: Crystallographic evidence of intramolecular nitrogen to phosphorus coordination [J].
Allen, DW ;
Hibbs, D ;
Hursthouse, MB ;
Malik, KMA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 572 (02) :259-264
[7]   Microwave-Promoted Palladium(II)-Catalyzed C-P Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates [J].
Andaloussi, Mounir ;
Lindh, Jonas ;
Savmarker, Jonas ;
Sjoberg, Per J. R. ;
Larhed, Mats .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :13069-13074
[8]  
[Anonymous], INDOLE ALKALOIDS
[9]  
[Anonymous], 2006, WO PCT Int. Appl., Patent No. 054182
[10]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]