Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds

doi:10.6023/cjoc202005089

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3380-3389.DOI: 10.6023/cjoc202005089 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

三脚架型二胺基-膦配体支撑的亚铁配合物与有机重氮化合物的反应

刘健, 肖洁, Sudipta Mondal, 冷雪冰, 邓亮

中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2020-05-29 修回日期:2020-06-27 发布日期:2020-07-01
通讯作者: 邓亮 E-mail:deng@sioc.ac.cn
基金资助:
科技部国家重点研发计划（No.2016YFA0202900）、国家自然科学基金（Nos.21725104，21690062，21821002）、中国科学院先导专项（No.XDB20000000）和上海市优秀学术带头人计划（No.19XD1424800）资助项目.

Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds

Liu Jian, Xiao Jie, Mondal Sudipta, Leng Xuebing, Deng Liang

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2020-05-29 Revised:2020-06-27 Published:2020-07-01
Supported by:
Project supported by the National Key Research and Development Program of the Ministry of Science and Technology (No. 2016YFA0202900), the Natural Science Foundation of China (Nos. 21725104, 21690062, 21821002), CAS Strategic Pilot Science And Technology Special (No. XDB20000000), and the Program of Shanghai Academic Research Leader (No. 19XD1424800).

1. cjoc202005089辅助材料.pdf(8170KB)

Abstract

Treatment of Bu^tPCl₂ with 2 equiv. of (2,4,6-Me₃C₆H₂)(2-LiC₆H₄)NLi and (2,6-Cl₂C₆H₃)(2-LiC₆H₄)NLi, which were generated in situ by the interaction of (2,4,6-Me₃C₆H₂)(2-BrC₆H₄)NH and (2,6-Cl₂C₆H₃)(2-BrC₆H₄)NH with 2 equiv. of BuⁿLi, followed by quenching with water, afforded new tridentate diamine-phosphine compounds (o-(N-(2,4,6-Me₃C₆H₂)-NH)C₆H₄)₂PBu^t and (o-(N-(2,6-Cl₂C₆H₃)NH)C₆H₄)₂PBu^t (denoted as H₂(^MesN₂P^Bu-t) and H₂(^dcpN₂P^Bu-t)), respectively. H₂(^MesN₂P^Bu-t) and H₂(^dcpN₂P^Bu-t) underwent amine-elimination reaction with[Fe(N(SiMe₃)₂)₂]₂ (0.5 equiv.) to afford iron(Ⅱ) complexes[(κ³-N,N,P-^MesN₂P^Bu-t)Fe(OEt₂)] (1) and[(κ³-N,N,P-^dcpN₂P^Bu-t)Fe(OEt₂)] (2) bearing tridentate diamido-phosphine ligands. Treatment of 1 with organic diazo compounds (p-tolyl)₂CN₂ and PhC(N₂)CO₂Et rendered the formation of diazo coordinated iron complexes[(κ³-N,N,P-^MesN₂P^Bu-t)Fe(η²-N,N-(p-tolyl)₂CN₂)] (3) and[(κ³-N,N,P-^MesN₂P^Bu-t)Fe(κ²-N,O-PhC(N₂)- CO₂Et)] (4), respectively. Complex 2 can catalyze the conversion of (p-tolyl)₂CN₂ to (p-tolyl)₂C=NN=C(tolyl-p)₂. Treatment of 2 with organic diazo compound DmpC(N₂)H rendered the formation of a high-spin iron(Ⅱ) complex featuring the tridentate bisamido-phosphine ylide ligand[(κ³-N,N,C-^dcpN₂P^Bu-tC^H,Dmp)Fe] (5). These complexes have been characterized by elemental analysis, ¹H NMR, solution magnetic susceptibility measurements, zero-field ⁵⁷Fe Mössbauer spectroscopy and single-crystal X-ray diffraction studies. The spectroscopic data in combination with theoretical study suggest that complex 3 can be viewed as a low-spin iron(IV) imido complex featuring an dianionic ligand[η²-N,N-(p-tolyl)₂CN₂]^2-, whereas 4 has an intermediate-spin iron(Ⅲ) center that is antiferromagnetically coupled to a diazoalkane radical anion[κ²-N,O-PhC(N₂)-CO₂Et)]^•1-.

Key words: iron, diazo compounds, diamido-phosphine ligand

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Liu Jian, Xiao Jie, Mondal Sudipta, Leng Xuebing, Deng Liang. Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3380-3389.

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三脚架型二胺基-膦配体支撑的亚铁配合物与有机重氮化合物的反应

Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds

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