Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands: Synthesis, structural diversity and characterization

Li Feng Hsueh; Min Hui Hsieh; Shu Ya Hsu; Cheng Yuan Lee; Hsiang Hua Hsieh; Amitabha Datta; Jui Hsien Huang; Chia Her Lin; Ting Yu Lee

doi:10.1002/jccs.201300611

Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands: Synthesis, structural diversity and characterization

Li Feng Hsueh
, Min Hui Hsieh
, Shu Ya Hsu
, Cheng Yuan Lee
, Hsiang Hua Hsieh
, Amitabha Datta
, Jui Hsien Huang^*
, Chia Her Lin
, Ting Yu Lee

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

A series of four, five and six-coordinated magnesium derivatives integrating with substituted pyrrole and ketimine ligands are conveniently synthesized. Reaction of two equiv of 2-dimethylaminomethyl pyrrole with Mg[N(SiMe₃)₂]₂ in THF affords the monomeric magnesium complex Mg[C₄H₃N(2-CH₂NMe ₂)]₂ (THF)₂ (1) in high yield along with elimination of two equiv of HN(SiMe₃)₂. Similarly, the reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe ₃)₂]₂ in THF renders the magnesium derivative, Mg[C₄H₃N(2-CH₂NH^tBu)] ₂(THF)2₂(2) in good yield. Interestingly, reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe₃) ₂]₂ in toluene, instead of THF, generates Mg[C ₄H₃N(2-CH2NH^tBu)]₂ (3), also in high yield. Furthermore, the assembly of two equiv of ketimine ligand, HOCMeCHCMeNAr (Ar = C₆H₃-2,6-ⁱPr₂) and Mg[N(SiMe₃)₂]₂, yields five-coordinated magnesium derivatives, Mg(OCMeCHCMeNAr)₂(THF) (4) and Mg(OCMeCHCMeNAr)₂(OEt₂) (5), using THF and diethyl ether, respectively. All the aforementioned derivatives are characterized by ¹H and ¹³C NMR spectroscopy as well as 1, 3, 4 and 5 are subjected to X-ray diffraction analysis in solid state.

Original language	English
Pages (from-to)	953-959
Number of pages	7
Journal	Journal of the Chinese Chemical Society
Volume	61
Issue number	8
DOIs	https://doi.org/10.1002/jccs.201300611
Publication status	Published - 2014 Aug
Externally published	Yes

Keywords

Ketiminate
Lewis base
Magnesium
Pyrrolyl

ASJC Scopus subject areas

General Chemistry

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10.1002/jccs.201300611

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@article{9462d8d5a7554d519ee99108974ed75c,

title = "Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands: Synthesis, structural diversity and characterization",

abstract = "A series of four, five and six-coordinated magnesium derivatives integrating with substituted pyrrole and ketimine ligands are conveniently synthesized. Reaction of two equiv of 2-dimethylaminomethyl pyrrole with Mg[N(SiMe3)2]2 in THF affords the monomeric magnesium complex Mg[C4H3N(2-CH2NMe 2)]2 (THF)2 (1) in high yield along with elimination of two equiv of HN(SiMe3)2. Similarly, the reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe 3)2]2 in THF renders the magnesium derivative, Mg[C4H3N(2-CH2NHtBu)] 2(THF)22(2) in good yield. Interestingly, reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe3) 2]2 in toluene, instead of THF, generates Mg[C 4H3N(2-CH2NHtBu)]2 (3), also in high yield. Furthermore, the assembly of two equiv of ketimine ligand, HOCMeCHCMeNAr (Ar = C6H3-2,6-iPr2) and Mg[N(SiMe3)2]2, yields five-coordinated magnesium derivatives, Mg(OCMeCHCMeNAr)2(THF) (4) and Mg(OCMeCHCMeNAr)2(OEt2) (5), using THF and diethyl ether, respectively. All the aforementioned derivatives are characterized by 1H and 13C NMR spectroscopy as well as 1, 3, 4 and 5 are subjected to X-ray diffraction analysis in solid state.",

keywords = "Ketiminate, Lewis base, Magnesium, Pyrrolyl",

author = "Hsueh, \{Li Feng\} and Hsieh, \{Min Hui\} and Hsu, \{Shu Ya\} and Lee, \{Cheng Yuan\} and Hsieh, \{Hsiang Hua\} and Amitabha Datta and Huang, \{Jui Hsien\} and Lin, \{Chia Her\} and Lee, \{Ting Yu\}",

year = "2014",

month = aug,

doi = "10.1002/jccs.201300611",

language = "English",

volume = "61",

pages = "953--959",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "John Wiley and Sons Inc.",

number = "8",

}

TY - JOUR

T1 - Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands

T2 - Synthesis, structural diversity and characterization

AU - Hsueh, Li Feng

AU - Hsieh, Min Hui

AU - Hsu, Shu Ya

AU - Lee, Cheng Yuan

AU - Hsieh, Hsiang Hua

AU - Datta, Amitabha

AU - Huang, Jui Hsien

AU - Lin, Chia Her

AU - Lee, Ting Yu

PY - 2014/8

Y1 - 2014/8

N2 - A series of four, five and six-coordinated magnesium derivatives integrating with substituted pyrrole and ketimine ligands are conveniently synthesized. Reaction of two equiv of 2-dimethylaminomethyl pyrrole with Mg[N(SiMe3)2]2 in THF affords the monomeric magnesium complex Mg[C4H3N(2-CH2NMe 2)]2 (THF)2 (1) in high yield along with elimination of two equiv of HN(SiMe3)2. Similarly, the reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe 3)2]2 in THF renders the magnesium derivative, Mg[C4H3N(2-CH2NHtBu)] 2(THF)22(2) in good yield. Interestingly, reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe3) 2]2 in toluene, instead of THF, generates Mg[C 4H3N(2-CH2NHtBu)]2 (3), also in high yield. Furthermore, the assembly of two equiv of ketimine ligand, HOCMeCHCMeNAr (Ar = C6H3-2,6-iPr2) and Mg[N(SiMe3)2]2, yields five-coordinated magnesium derivatives, Mg(OCMeCHCMeNAr)2(THF) (4) and Mg(OCMeCHCMeNAr)2(OEt2) (5), using THF and diethyl ether, respectively. All the aforementioned derivatives are characterized by 1H and 13C NMR spectroscopy as well as 1, 3, 4 and 5 are subjected to X-ray diffraction analysis in solid state.

AB - A series of four, five and six-coordinated magnesium derivatives integrating with substituted pyrrole and ketimine ligands are conveniently synthesized. Reaction of two equiv of 2-dimethylaminomethyl pyrrole with Mg[N(SiMe3)2]2 in THF affords the monomeric magnesium complex Mg[C4H3N(2-CH2NMe 2)]2 (THF)2 (1) in high yield along with elimination of two equiv of HN(SiMe3)2. Similarly, the reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe 3)2]2 in THF renders the magnesium derivative, Mg[C4H3N(2-CH2NHtBu)] 2(THF)22(2) in good yield. Interestingly, reaction between two equiv of 2-t-butylaminomethyl pyrrole and Mg[N(SiMe3) 2]2 in toluene, instead of THF, generates Mg[C 4H3N(2-CH2NHtBu)]2 (3), also in high yield. Furthermore, the assembly of two equiv of ketimine ligand, HOCMeCHCMeNAr (Ar = C6H3-2,6-iPr2) and Mg[N(SiMe3)2]2, yields five-coordinated magnesium derivatives, Mg(OCMeCHCMeNAr)2(THF) (4) and Mg(OCMeCHCMeNAr)2(OEt2) (5), using THF and diethyl ether, respectively. All the aforementioned derivatives are characterized by 1H and 13C NMR spectroscopy as well as 1, 3, 4 and 5 are subjected to X-ray diffraction analysis in solid state.

KW - Ketiminate

KW - Lewis base

KW - Magnesium

KW - Pyrrolyl

UR - https://www.scopus.com/pages/publications/84906303855

UR - https://www.scopus.com/pages/publications/84906303855#tab=citedBy

U2 - 10.1002/jccs.201300611

DO - 10.1002/jccs.201300611

M3 - Article

AN - SCOPUS:84906303855

SN - 0009-4536

VL - 61

SP - 953

EP - 959

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 8

ER -

Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands: Synthesis, structural diversity and characterization

Abstract

Keywords

ASJC Scopus subject areas

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