Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions

Bilel Hamzaoui; Jeremie Pelletier; Mohamad El Eter; Yin Chen; Edy Abou-Hamad; Jean-Marie Basset

doi:10.1002/adsc.201500484

Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions

Bilel Hamzaoui, Jeremie Pelletier, Mohamad El Eter, Yin Chen, Edy Abou-Hamad, Jean-Marie Basset

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

25 Scopus citations

Abstract

Intermolecular catalytic hydroaminoalkylation of unactivated alkene occurs with silica-supported azazirconacyclopropane [[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)(η2-NMeCH2)(NMe2)]. Mechanistic studies were conducted using surface organometallic chemistry (SOMC) concepts to identify the key surface intermediates. The azametallacyclopentene intermediate {[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)[η2-NMeCH2CH(Me)CH2](NMe2)} was isolated after treating with 1-propylene and characterized by FT-IR spectroscopy, elemental analysis, 1H 13C HETCOR, DARR SS-NMR and DQ TQ SS-NMR. The regeneration of the catalyst was conducted by dimethylamine protonolysis to yield the pure amine.

Original language	English (US)
Pages (from-to)	3148-3154
Number of pages	7
Journal	Advanced Synthesis & Catalysis
Volume	357
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201500484
State	Published - Sep 25 2015

ASJC Scopus subject areas

Organic Chemistry
Catalysis

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https://repository.kaust.edu.sa/bitstream/10754/578864/1/Hamzaoui_et_al-2015-Advanced_Synthesis_and_Catalysis.pdf

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title = "Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions",

abstract = "Intermolecular catalytic hydroaminoalkylation of unactivated alkene occurs with silica-supported azazirconacyclopropane [[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)(η2-NMeCH2)(NMe2)]. Mechanistic studies were conducted using surface organometallic chemistry (SOMC) concepts to identify the key surface intermediates. The azametallacyclopentene intermediate {[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)[η2-NMeCH2CH(Me)CH2](NMe2)} was isolated after treating with 1-propylene and characterized by FT-IR spectroscopy, elemental analysis, 1H 13C HETCOR, DARR SS-NMR and DQ TQ SS-NMR. The regeneration of the catalyst was conducted by dimethylamine protonolysis to yield the pure amine.",

author = "Bilel Hamzaoui and Jeremie Pelletier and {El Eter}, Mohamad and Yin Chen and Edy Abou-Hamad and Jean-Marie Basset",

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language = "English (US)",

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T1 - Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions

AU - Hamzaoui, Bilel

AU - Pelletier, Jeremie

AU - El Eter, Mohamad

AU - Chen, Yin

AU - Abou-Hamad, Edy

AU - Basset, Jean-Marie

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2015/9/25

Y1 - 2015/9/25

N2 - Intermolecular catalytic hydroaminoalkylation of unactivated alkene occurs with silica-supported azazirconacyclopropane [[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)(η2-NMeCH2)(NMe2)]. Mechanistic studies were conducted using surface organometallic chemistry (SOMC) concepts to identify the key surface intermediates. The azametallacyclopentene intermediate {[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)[η2-NMeCH2CH(Me)CH2](NMe2)} was isolated after treating with 1-propylene and characterized by FT-IR spectroscopy, elemental analysis, 1H 13C HETCOR, DARR SS-NMR and DQ TQ SS-NMR. The regeneration of the catalyst was conducted by dimethylamine protonolysis to yield the pure amine.

AB - Intermolecular catalytic hydroaminoalkylation of unactivated alkene occurs with silica-supported azazirconacyclopropane [[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)(η2-NMeCH2)(NMe2)]. Mechanistic studies were conducted using surface organometallic chemistry (SOMC) concepts to identify the key surface intermediates. The azametallacyclopentene intermediate {[TRIPLE BOND]Si[BOND]O[BOND]Zr(HNMe2)[η2-NMeCH2CH(Me)CH2](NMe2)} was isolated after treating with 1-propylene and characterized by FT-IR spectroscopy, elemental analysis, 1H 13C HETCOR, DARR SS-NMR and DQ TQ SS-NMR. The regeneration of the catalyst was conducted by dimethylamine protonolysis to yield the pure amine.

UR - http://hdl.handle.net/10754/578864

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DO - 10.1002/adsc.201500484

M3 - Article

SN - 1615-4150

VL - 357

SP - 3148

EP - 3154

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 14-15

ER -

Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions

Abstract

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