Generation of Cyclopentadiene for Diels-Alder Reactions by Visible-Light Irradiation of Iron Sandwich Complexes

被引:3
作者
Sokolov, Alexey S. [1 ]
Polezhaev, Alexander, V [1 ]
Nelyubina, Yulia, V [1 ]
Perekalin, Dmitry S. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova 28, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
cyclopentadiene; Diels-Alder reaction; iron; photochemistry; sandwich complexes; ARENE REPLACEMENT REACTIONS; TRIPLE-DECKER COMPLEXES; PHOTOCHEMICAL-REACTION; LIGAND; ROUTE; DECOMPOSITION; REACTIVITY; ORGANOIRON; CHEMISTRY; BOND;
D O I
10.1002/hlca.202100246
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclopentadienes readily undergo fast and selective Diels-Alder reactions which can be used for conjugation of biomolecules and polymers. Herein we present a new method for the photochemical generation of cyclopentadienes by the visible light irradiation of the iron complexes [(C5H4R)Fe(arene)](+). This reaction proceeds at room temperature, in water, and in the presence of potentially interfering amino acids. Free cyclopentadiene is trapped by dienophiles to give the corresponding Diels-Alder adducts in 72-95 % yield.
引用
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页数:8
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[1]  
Abd-El-Aziz AS, 2002, MACROMOL RAPID COMM, V23, P113
[2]   Synthesis and reactivity of arenes coordinated to cyclopentadienyliron cations [J].
Abd-El-Aziz, AS ;
Bernardin, S .
COORDINATION CHEMISTRY REVIEWS, 2000, 203 :219-267
[3]   Synthesis of 7-norbornenols via Diels-Alder cycloadditions of cyclopentadienol generated by decomposition of ferrocenium cation [J].
Allen, Stacey K. ;
Lathrop, Thomas E. ;
Patel, Sweta B. ;
Moody, Deanna M. Harrell ;
Sommer, Roger D. ;
Coombs, Thomas C. .
TETRAHEDRON LETTERS, 2015, 56 (44) :6038-6042
[4]   Simple synthesis of organo-iron complexes from iron-sandwich raw materials using visible light [J].
Aranzaes, Jaime Ruiz ;
Astruc, Didier .
INORGANICA CHIMICA ACTA, 2008, 361 (01) :1-4
[5]   Metallocenyl dendrimers and their applications in molecular electronics, sensing, and catalysis [J].
Astruc, Didier ;
Ornelas, Catia ;
Ruiz, Jaime .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (07) :841-856
[6]   Shining Light on Cyclopentadienone-Norbornadiene Diels-Alder Adducts to Enable Photoinduced Click Chemistry with Cyclopentadiene [J].
Bailey, Sophia J. ;
Stricker, Friedrich ;
Hopkins, Erik ;
Wilson, Maxwell Z. ;
de Alaniz, Javier Read .
ACS APPLIED MATERIALS & INTERFACES, 2021, 13 (30) :35422-35430
[7]   Synthesis of cyclopentadiene derivatives by retro-Diels-Alder reaction of norbornadiene derivatives [J].
Dalkilic, Erdin ;
Dastan, Arif .
TETRAHEDRON, 2015, 71 (13) :1966-1970
[8]   New, Simple Synthetic Route to Functional Mono- and Biferrocenes [J].
Diallo, Abdou Khadri ;
Ruiz, Jaime ;
Astruc, Didier .
INORGANIC CHEMISTRY, 2010, 49 (04) :1913-1920
[9]   Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of -Hydroxylactams and Lactams [J].
Ding, Guangni ;
Li, Chengjun ;
Shen, Yifan ;
Lu, Bin ;
Zhang, Zhaoguo ;
Xie, Xiaomin .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) :1241-1250
[10]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341