Versatile reactions of a para-bromophenylacetylide iron(II) derivative and X-ray structure of the fluoro analogue. Synthesis of new redox-active organoiron(II) synthons

Courmarcel J.; Le Gland G.; Toupet L.; Paul F.; Lapinte C.

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Versatile reactions of a para-bromophenylacetylide iron(II) derivative and X-ray structure of the fluoro analogue. Synthesis of new redox-active organoiron(II) synthons

机译：对溴苯基乙炔铁（II）衍生物和氟类似物的X射线结构的多功能反应。新型氧化还原活性有机铁（II）合成子的合成

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The synthesis of the new (eta(2)-dppe)(n(5)-C5Me5)Fe-CdropC-1,3-(C6H4X) (m-2a/2b; X = F/Br) and (n(2)-dppe)(eta(5)-C5Me5)Fe-CdropC-1,4-(C6H4F) (2a) (2c) complexes, as well as the solid-state structure of the known (eta(2)-dppe)(eta(5)-C5Me5)Fe-CdropC-1,4-(C6H4F) (2a) complex are described. The catalytic coupling reactions of the bromo complexes with various alkynes were next investigated. Starting from the known (eta(2)-dppe)(eta(5)-C5Me5)Fe-CdropC-1,4-(C6H4Br) complex (2b), the synthesis of the (eta(2)-dppe)(eta(5)-C5Me5)FeCdropC-1,4-(C6H4)-CdropC-H complex (6d) and of the corresponding silyl-protected precursors (eta(2)-dppe)(eta(5)-C5Me5)Fe-CdropC-1,4-(C6H4)CdropC-SiR3 (6b/6c; R = Pr-1/Me) are reported. By use of lithium-bromine exchange reactions on 2b, the silyl-(7a; E = Si; R = Me) and tin- (7b-7d; E = Sn; R = Me, Bu, Ph) substituted analogues (eta(2)-dppe)(eta(5)-C5Me5)Fe-CdropC-1,4-(C6H4)ER3 are also isolated. The spectroscopic and electrochemical characterisations of all these new Fe(II)/Fe(III) redox-active building blocks are presented and the electronic substituent parameters for the ''(eta(2)-dppe)(eta(5)-C5Me5)Fe-CdropC" group are determined by means of F-19-NMR. (C) 2002 Elsevier Science B.V. All rights reserved. [References: 90]

机译：新（eta（2）-dppe）（n（5）-C5Me5）Fe-CdropC-1,3-（C6H4X）（m-2a / 2b; X = F / Br）和（n（2 ）-dppe）（eta（5）-C5Me5）Fe-CdropC-1,4-（C6H4F）（2a）（2c）配合物，以及已知（eta（2）-dppe）的固态结构描述了（eta（5）-C5Me5）Fe-CdropC-1,4-（C6H4F）（2a）配合物。接下来研究溴配合物与各种炔烃的催化偶联反应。从已知的（eta（2）-dppe）（eta（5）-C5Me5）Fe-CdropC-1,4-（C6H4Br）络合物（2b）开始，合成（eta（2）-dppe）（eta （5）-C5Me5）FeCdropC-1,4-（C6H4）-CdropC-H配合物（6d）和相应的甲硅烷基保护的前体（eta（2）-dppe）（eta（5）-C5Me5）Fe-CdropC报告了-1,4-（C6H4）CdropC-SiR3（6b / 6c; R = Pr-1 / Me）。通过在2b上进行溴化锂交换反应，甲硅烷基-（7a; E = Si; R = Me）和锡-（7b-7d; E = Sn; R = Me，Bu，Ph）取代的类似物（eta（还分离出2）-dppe）（eta（5）-C5Me5）Fe-CdropC-1,4-（C6H4）ER3。提出了所有这些新的Fe（II）/ Fe（III）氧化还原活性结构单元的光谱和电化学特性，并给出了``（eta（2）-dppe）（eta（5）-C5Me5）的电子取代基参数Fe-CdropC”基团通过F-19-NMR测定。（C）2002 Elsevier Science BV保留所有权利。[参考文献：90]

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《Journal of Organometallic Chemistry》 |2003年第2期|共15页
作者
Courmarcel J.; Le Gland G.; Toupet L.; Paul F.; Lapinte C.;
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正文语种 eng
中图分类有机化学;
关键词
Aryl halides; Organoiron; Acetylides; Redox-active; Synthesis; Hammett; Nonlinear-optical properties; Transition-metal complexes; Molecular-scale wires; Functional aryl group; Acetylide complexes; Sigma-acetylides; Organometallic complexes; Organic electrophiles; Ruthenium complexes; Organotin reagents;

机译：芳基卤化物;有机铁;乙炔化物;氧化还原活性;合成;Hammett;非线性光学性质;过渡金属配合物;分子线;功能性芳基;乙内酰胺配合物;西格玛乙炔;有机金属配合物;有机亲电试剂;钌配合物;有机锡试剂;

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1. Versatile reactions of a para-bromophenylacetylide iron(II) derivative and X-ray structure of the fluoro analogue. Synthesis of new redox-active organoiron(II) synthons [J] . Courmarcel J., Le Gland G., Toupet L., Journal of Organometallic Chemistry . 2003,第1a2期

机译：对溴苯基乙炔铁（II）衍生物和氟类似物的X射线结构的多功能反应。新型氧化还原活性有机铁（II）合成子的合成
2. Free-radical reactions of the tris-dioximate clathrochelates: synthesis and X-ray structure of the first cyclohexyl-substituted monoribbed-functionalized macrobicyclic iron(II) complex [J] . A. B. Burdukov, M. A. Vershinin, N. V. Pervukhina Russian Chemical Bulletin . 2011,第12期

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3. Mono- and bis(hydrazine) complexes of osmium(II): Synthesis, reactions, and X-ray crystal structure of the [Os(NH2NH2)(2){P(OEt)(3)}(4)](BPh4)(2) derivative [J] . Albertin G., Bacchi A., Bergano M., Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 1998,第3期

机译：II（II）的单和双（肼）配合物：[Os（NH2NH2）（2）{P（OEt）（3）}（4）]（BPh4）的合成，反应和X射线晶体结构（2）导数
4. SYNTHESIS OF 2,3-DIHYDROBENZOFURAN DERIVATIVES VIA ELECTRON TRANSFER REACTION CATALYZED BY IRON(III)-SALT IN AN IONIC LIQUID SOLVENT SYSTEM [C] . Toshiyuki Itoh, Hiroyuki Uehara, Kimio Kawai, Proceedings vol.2004-10; International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda and Meeting of the Electrochemical Society; 20040509-14; San Antonio,TX(US) . 2004

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Versatile reactions of a para-bromophenylacetylide iron(II) derivative and X-ray structure of the fluoro analogue. Synthesis of new redox-active organoiron(II) synthons

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