Inorganic–organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction
Bis(1-phenylethanaminium) disulfatotetraaquazincate(II) dihydrate (C8H12N)2[Zn(H2O)4(SO4)2]·2H2O (1), bis(1H-benzo[d]imidazolium) hexaaquazinc(II) bis(sulfate) tetrahydrate (C7H7N2)2[Zn(H2O)6](SO4)2·4H2O (2) and bis(2-methyl-1H-imidazolium) hexaaquazinc(II) bis(sulfate) dihydrate (C4H7N2)2[Zn(H2O)6]...
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| Veröffentlicht in: | Journal of organometallic chemistry 2013-10, Vol.741-742, p.136-140 |
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| container_title | Journal of organometallic chemistry |
| container_volume | 741-742 |
| creator | Kammoun, Omar Rekik, Walid Bataille, Thierry Mahmudov, Kamran T. Kopylovich, Maximilian N. Naïli, Houcine |
| description | Bis(1-phenylethanaminium) disulfatotetraaquazincate(II) dihydrate (C8H12N)2[Zn(H2O)4(SO4)2]·2H2O (1), bis(1H-benzo[d]imidazolium) hexaaquazinc(II) bis(sulfate) tetrahydrate (C7H7N2)2[Zn(H2O)6](SO4)2·4H2O (2) and bis(2-methyl-1H-imidazolium) hexaaquazinc(II) bis(sulfate) dihydrate (C4H7N2)2[Zn(H2O)6](SO4)2·2H2O (3) have been synthesized and fully structurally characterized including single-crystal X-ray diffraction analysis. 1–3 are organically templated hybrid layered materials comprising aquazinc(II) and aminium cations and sulfate anions. 1–3 are effective catalysts in the asymmetric Henry reaction; 1 being the most efficient one (yields up to 85% and threo/erythro diastereoselectivity up to 89:11).
New inorganic–organic hybrid materials effectively and diastereoselectively catalyze the C–C bond formation upon nitroaldol (Henry) reaction. [Display omitted]
•New hybrid materials were easily prepared from zinc(II) salt, sulfuric acid and amines.•Full structural characterization of the compounds was performed.•The synthesized compounds act as effective catalysts in the nitroaldol (Henry) reaction. |
| doi_str_mv | 10.1016/j.jorganchem.2013.05.028 |
| format | Article |
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New inorganic–organic hybrid materials effectively and diastereoselectively catalyze the C–C bond formation upon nitroaldol (Henry) reaction. [Display omitted]
•New hybrid materials were easily prepared from zinc(II) salt, sulfuric acid and amines.•Full structural characterization of the compounds was performed.•The synthesized compounds act as effective catalysts in the nitroaldol (Henry) reaction.</description><identifier>ISSN: 0022-328X</identifier><identifier>EISSN: 1872-8561</identifier><identifier>EISSN: 0022-328X</identifier><identifier>DOI: 10.1016/j.jorganchem.2013.05.028</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Chemical Sciences ; Crystal structures ; Diastereoselectivity ; Double salts ; Henry reaction ; Hybrid materials ; Other</subject><ispartof>Journal of organometallic chemistry, 2013-10, Vol.741-742, p.136-140</ispartof><rights>2013 Elsevier B.V.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c332t-1a987a13f17ccdd8479a167f0743167e87500039f4c1addfc22599743a3719143</citedby><cites>FETCH-LOGICAL-c332t-1a987a13f17ccdd8479a167f0743167e87500039f4c1addfc22599743a3719143</cites><orcidid>0000-0002-9224-5851 ; 0000-0002-0156-9317</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0022328X13004154$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://univ-rennes.hal.science/hal-00860183$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Kammoun, Omar</creatorcontrib><creatorcontrib>Rekik, Walid</creatorcontrib><creatorcontrib>Bataille, Thierry</creatorcontrib><creatorcontrib>Mahmudov, Kamran T.</creatorcontrib><creatorcontrib>Kopylovich, Maximilian N.</creatorcontrib><creatorcontrib>Naïli, Houcine</creatorcontrib><title>Inorganic–organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction</title><title>Journal of organometallic chemistry</title><description>Bis(1-phenylethanaminium) disulfatotetraaquazincate(II) dihydrate (C8H12N)2[Zn(H2O)4(SO4)2]·2H2O (1), bis(1H-benzo[d]imidazolium) hexaaquazinc(II) bis(sulfate) tetrahydrate (C7H7N2)2[Zn(H2O)6](SO4)2·4H2O (2) and bis(2-methyl-1H-imidazolium) hexaaquazinc(II) bis(sulfate) dihydrate (C4H7N2)2[Zn(H2O)6](SO4)2·2H2O (3) have been synthesized and fully structurally characterized including single-crystal X-ray diffraction analysis. 1–3 are organically templated hybrid layered materials comprising aquazinc(II) and aminium cations and sulfate anions. 1–3 are effective catalysts in the asymmetric Henry reaction; 1 being the most efficient one (yields up to 85% and threo/erythro diastereoselectivity up to 89:11).
New inorganic–organic hybrid materials effectively and diastereoselectively catalyze the C–C bond formation upon nitroaldol (Henry) reaction. [Display omitted]
•New hybrid materials were easily prepared from zinc(II) salt, sulfuric acid and amines.•Full structural characterization of the compounds was performed.•The synthesized compounds act as effective catalysts in the nitroaldol (Henry) reaction.</description><subject>Chemical Sciences</subject><subject>Crystal structures</subject><subject>Diastereoselectivity</subject><subject>Double salts</subject><subject>Henry reaction</subject><subject>Hybrid materials</subject><subject>Other</subject><issn>0022-328X</issn><issn>1872-8561</issn><issn>0022-328X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkEtOwzAQhi0EEuVxB29ZJPiRh7MsFVCkSmxAYmdN7QlxFWJkh0rdcQcuwFk4CifBpQiWrP7RzP-PZj5CKGc5Z7w6X-UrHx5hMB0-5YJxmbMyZ0LtkQlXtchUWfF9MmFMiEwK9XBIjmJcMZacTE3I483wHXfm8_Xtp6LdZhmcpda_LHuk8aVvYcRIIVIDI_SbOEbq24_3scOPd-sgjhjQR-zRjG6NdHBj8NBb39OAkHp-OCEHLfQRT3_0mNxfXd7N5tni9vpmNl1kRkoxZhwaVQOXLa-NsVYVdQO8qltWFzIpqrpMp8umLQwHa1sjRNk0aQiy5g0v5DE52-3toNfPwT1B2GgPTs-nC73tMaYqxpVc8-RVO68JPsaA7W-AM72Fq1f6D67ewtWs1Aluil7soph-WTsMOhqHg0HrQoKgrXf_L_kC5iKL_w</recordid><startdate>20131001</startdate><enddate>20131001</enddate><creator>Kammoun, Omar</creator><creator>Rekik, Walid</creator><creator>Bataille, Thierry</creator><creator>Mahmudov, Kamran T.</creator><creator>Kopylovich, Maximilian N.</creator><creator>Naïli, Houcine</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-9224-5851</orcidid><orcidid>https://orcid.org/0000-0002-0156-9317</orcidid></search><sort><creationdate>20131001</creationdate><title>Inorganic–organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction</title><author>Kammoun, Omar ; Rekik, Walid ; Bataille, Thierry ; Mahmudov, Kamran T. ; Kopylovich, Maximilian N. ; Naïli, Houcine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c332t-1a987a13f17ccdd8479a167f0743167e87500039f4c1addfc22599743a3719143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Chemical Sciences</topic><topic>Crystal structures</topic><topic>Diastereoselectivity</topic><topic>Double salts</topic><topic>Henry reaction</topic><topic>Hybrid materials</topic><topic>Other</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kammoun, Omar</creatorcontrib><creatorcontrib>Rekik, Walid</creatorcontrib><creatorcontrib>Bataille, Thierry</creatorcontrib><creatorcontrib>Mahmudov, Kamran T.</creatorcontrib><creatorcontrib>Kopylovich, Maximilian N.</creatorcontrib><creatorcontrib>Naïli, Houcine</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Journal of organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kammoun, Omar</au><au>Rekik, Walid</au><au>Bataille, Thierry</au><au>Mahmudov, Kamran T.</au><au>Kopylovich, Maximilian N.</au><au>Naïli, Houcine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inorganic–organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction</atitle><jtitle>Journal of organometallic chemistry</jtitle><date>2013-10-01</date><risdate>2013</risdate><volume>741-742</volume><spage>136</spage><epage>140</epage><pages>136-140</pages><issn>0022-328X</issn><eissn>1872-8561</eissn><eissn>0022-328X</eissn><abstract>Bis(1-phenylethanaminium) disulfatotetraaquazincate(II) dihydrate (C8H12N)2[Zn(H2O)4(SO4)2]·2H2O (1), bis(1H-benzo[d]imidazolium) hexaaquazinc(II) bis(sulfate) tetrahydrate (C7H7N2)2[Zn(H2O)6](SO4)2·4H2O (2) and bis(2-methyl-1H-imidazolium) hexaaquazinc(II) bis(sulfate) dihydrate (C4H7N2)2[Zn(H2O)6](SO4)2·2H2O (3) have been synthesized and fully structurally characterized including single-crystal X-ray diffraction analysis. 1–3 are organically templated hybrid layered materials comprising aquazinc(II) and aminium cations and sulfate anions. 1–3 are effective catalysts in the asymmetric Henry reaction; 1 being the most efficient one (yields up to 85% and threo/erythro diastereoselectivity up to 89:11).
New inorganic–organic hybrid materials effectively and diastereoselectively catalyze the C–C bond formation upon nitroaldol (Henry) reaction. [Display omitted]
•New hybrid materials were easily prepared from zinc(II) salt, sulfuric acid and amines.•Full structural characterization of the compounds was performed.•The synthesized compounds act as effective catalysts in the nitroaldol (Henry) reaction.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.jorganchem.2013.05.028</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9224-5851</orcidid><orcidid>https://orcid.org/0000-0002-0156-9317</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Chemical Sciences Crystal structures Diastereoselectivity Double salts Henry reaction Hybrid materials Other |
| title | Inorganic–organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction |
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