NDLI: Reactivity of functionalized indoles with rare-earth metal amides. Synthesis, characterization and catalytic activity of rare-earth metal complexes incorporating indolyl ligands

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Zhou, Shuangliu Guo, Liping Wei, Yun Zhang, Guangchao Wang, Shaowu Feng, Zhijun Mu, Xiaolong Zhu, Xiancui
Description	Author Affiliation: Feng Z ( Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, P. R. China. swwang@mail.ahnu.edu.cn.)
Abstract	The reactivity of several functionalized indoles $2-(RNHCH_{2})C_{8}H_{5}NH$ (R = $C_{6}H_{5}$ (1), $^{t}Bu$ (2), $2,6-^{i}Pr_{2}C_{6}H_{3}$ (3)) with rare-earth metal amides is described. Reactions of 1 or 2 with $[(Me_{3}Si)_{2}N]_{3}RE(μ-Cl)Li(THF)_{3}$ (RE = Eu, Yb) respectively produced the europium complexes $[2-(C_{6}H_{5}N=CH)C_{8}H_{5}N]_{2}Eu[N(SiMe_{3})_{2}]$ (4) and $[2-(^{t}BuN=CH)C_{8}H_{5}N]Eu[N(SiMe_{3})_{2}]_{2}$ (5), and the ytterbium complex $[2-(^{t}BuN=CH)C_{8}H_{5}N]_{2}Yb[N(SiMe_{3})_{2}]$ (6), containing bidentate anionic indolyl ligands via dehydrogenation of the amine to the imine. In contrast, reactions of the more sterically bulky indole 3 with $[(Me_{3}Si)_{2}N]_{3}RE(μ-Cl)Li(THF)_{3}$ afforded complexes $[2-(2,6-^{i}Pr_{2}C_{6}H_{3}NCH_{2})C_{8}H_{5}N]RE[N(SiMe_{3})_{2}](THF)_{2}$ (RE = Yb (7), Y (8), Er (9), Dy (10)) with the deprotonated indolyl ligand. While reactions of 3 with yttrium and ytterbium amides in refluxing toluene respectively gave the complexes $[2-(2,6-^{i}Pr_{2}C_{6}H_{3}N=CH)C_{8}H_{5}N]_{3}Y$ (11) and $[2-(2,6-^{i}Pr_{2}C_{6}H_{3}N=CH)C_{8}H_{5}N]_{2}Yb^{II}(THF)_{2}$ (12), along with transformation of the amino group to the imino group, and also with a reduction of $Yb^{3+}$ to $Yb^{2+}$ in the formation of 12. Reactions of 3 with samarium and neodymium amides provided novel dinuclear complexes $\{[μ–η^{5}:η^{1}:η^{1}-2-(2,6-^{i}Pr_{2}C_{6}H_{3}NCH_{2})C_{8}H_{5}N]RE[N(SiMe_{3})_{2}]\}_{2}$ (RE = Sm (13), Nd (14)) having indolyl ligands in $μ–η^{5}:η^{1}:η^{1}$ hapticities. The pathway for the transformation of the amino group to the imino group is proposed on the basis of the experimental results. The new complexes displayed excellent activity in the intramolecular hydroamination of aminoalkenes.
ISSN	14779226
Issue Number	47
Journal	Dalton Trans.
Volume Number	44
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2015-12-21
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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