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

Research output: Contribution to journalArticle

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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.

Original languageEnglish
Pages (from-to)953-959
Number of pages7
JournalJournal of the Chinese Chemical Society
Volume61
Issue number8
DOIs
Publication statusPublished - 2014 Aug

Fingerprint

Lewis Bases
Pyrroles
Magnesium
Ligands
Derivatives
Toluene
Ether
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Hsueh, Li Feng ; Hsieh, Min Hui ; Hsu, Shu Ya ; Lee, Cheng Yuan ; Hsieh, Hsiang Hua ; Datta, Amitabha ; Huang, Jui Hsien ; Lin, Chia Her ; Lee, Ting Yu. / Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands : Synthesis, structural diversity and characterization. In: Journal of the Chinese Chemical Society. 2014 ; Vol. 61, No. 8. pp. 953-959.
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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.",
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}",
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language = "English",
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Lewis base assisted magnesium complexes incorporating pyrrolyl and ketiminate ligands : Synthesis, structural diversity and characterization. / Hsueh, Li Feng; Hsieh, Min Hui; Hsu, Shu Ya; Lee, Cheng Yuan; Hsieh, Hsiang Hua; Datta, Amitabha; Huang, Jui Hsien; Lin, Chia Her; Lee, Ting Yu.

In: Journal of the Chinese Chemical Society, Vol. 61, No. 8, 08.2014, p. 953-959.

Research output: Contribution to journalArticle

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.

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U2 - 10.1002/jccs.201300611

DO - 10.1002/jccs.201300611

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