Facile Synthesis of Cooperative Acid-Base Catalysts by Clicking Cysteine and Cysteamine on an Ethylene-Bridged Periodic Mesoporous Organosilica

A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid–base catalysts. A straightforward, single‐step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol‐ene...

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Published in:	European journal of inorganic chemistry Vol. 2016; no. 13-14; pp. 2144 - 2151
Main Authors:	Ouwehand, Judith, Lauwaert, Jeroen, Esquivel, Dolores, Hendrickx, Kevin, Van Speybroeck, Veronique, Thybaut, Joris W., Van Der Voort, Pascal
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 01.05.2016 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Subjects:	Acids Aldehydes Aldol reactions Amines Amino acids Carboxylic acids Catalysis Catalysts Chemical reactions Click chemistry Cysteamine Cysteine Heterogeneous catalysis Mesoporous materials
ISSN:	1434-1948, 1099-0682
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Abstract	A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid–base catalysts. A straightforward, single‐step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol‐ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4‐nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine‐functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study. An ethylene‐bridged periodic mesoporous organosilica was functionalized with cysteine and cysteamine by means of thiol‐ene click chemistry. The resulting cooperative acid–base catalysts were tested for their activity in an aldol reaction. The influence of the acid promoting sites as well as the loading of the active centers is discussed herein.
AbstractList	A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid–base catalysts. A straightforward, single‐step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol‐ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4‐nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine‐functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study. An ethylene‐bridged periodic mesoporous organosilica was functionalized with cysteine and cysteamine by means of thiol‐ene click chemistry. The resulting cooperative acid–base catalysts were tested for their activity in an aldol reaction. The influence of the acid promoting sites as well as the loading of the active centers is discussed herein. A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid–base catalysts. A straightforward, single‐step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol‐ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4‐nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine‐functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study. A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid-base catalysts. A straightforward, single-step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol-ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4-nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine-functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study. An ethylene-bridged periodic mesoporous organosilica was functionalized with cysteine and cysteamine by means of thiol-ene click chemistry. The resulting cooperative acid-base catalysts were tested for their activity in an aldol reaction. The influence of the acid promoting sites as well as the loading of the active centers is discussed herein.
Author	Hendrickx, Kevin Esquivel, Dolores Ouwehand, Judith Thybaut, Joris W. Van Der Voort, Pascal Lauwaert, Jeroen Van Speybroeck, Veronique
Author_xml	– sequence: 1 givenname: Judith surname: Ouwehand fullname: Ouwehand, Judith organization: Department of Inorganic and Physical Chemistry, Ghent University Krijgslaan 281-S3, 9000 Ghent, Belgium, http://www.comoc.ugent.be – sequence: 2 givenname: Jeroen surname: Lauwaert fullname: Lauwaert, Jeroen organization: Department of Chemical Technology, Ghent University Technologiepark 914, 9052 Ghent, Belgium – sequence: 3 givenname: Dolores surname: Esquivel fullname: Esquivel, Dolores organization: Department of Inorganic and Physical Chemistry, Ghent University Krijgslaan 281-S3, 9000 Ghent, Belgium, http://www.comoc.ugent.be – sequence: 4 givenname: Kevin surname: Hendrickx fullname: Hendrickx, Kevin organization: Department of Inorganic and Physical Chemistry, Ghent University Krijgslaan 281-S3, 9000 Ghent, Belgium, http://www.comoc.ugent.be – sequence: 5 givenname: Veronique surname: Van Speybroeck fullname: Van Speybroeck, Veronique organization: Center for Molecular Modeling, Ghent University Technologiepark 903, 9052 Zwijnaarde, Belgium – sequence: 6 givenname: Joris W. surname: Thybaut fullname: Thybaut, Joris W. organization: Department of Chemical Technology, Ghent University Technologiepark 914, 9052 Ghent, Belgium – sequence: 7 givenname: Pascal surname: Van Der Voort fullname: Van Der Voort, Pascal email: pascal.vandervoort@ugent.be organization: Department of Inorganic and Physical Chemistry, Ghent University Krijgslaan 281-S3, 9000 Ghent, Belgium, http://www.comoc.ugent.be
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References_xml	– reference: M. Sharifi , C. Köhler , P. Tölle , T. Frauenheim , M. Wark , Small 2011 , 7 , 1086 -1097 . – reference: N. A. Brunelli , K. Venkatasubbaiah , C. W. Jones , Chem. Mater. 2012 , 24 , 2433 -2442 . – reference: J. Lauwaert , E. G. Moschetta , P. Van Der Voort , J. W. Thybaut , C. W. Jones , G. B. Marin , J. Catal. 2015 , 325 , 19 -25 . – reference: G. Lippert , J. Hutter , M. Parrinello , Mol. Phys. 1997 , 92 , 477 -487 . – reference: J. Lauwaert , E. De Canck , D. Esquivel , J. W. Thybaut , P. Van Der Voort , G. B. Marin , ChemCatChem 2014 , 6 , 255 -264 . – reference: S. Shylesh , A. Wagener , A. Seifert , S. Ernst , W. R. Thiel , Angew. Chem. Int. Ed. 2010 , 49 , 184 -187 ; Angew. Chem. 2010 , 122 , 188 . – reference: R. Krishnan , J. Binkley , R. Seeger , J. Pople , J. Chem. Phys. 1980 , 72 , 650 -654 . – reference: J. C. Hicks , R. Dabestani , A. C. Buchanan , C. W. Jones , Chem. Mater. 2006 , 18 , 5022 -5032 . – reference: S. Nosé , J. Chem. 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Snippet	A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid–base catalysts. A... A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid-base catalysts. A...
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StartPage	2144
SubjectTerms	Acids Aldehydes Aldol reactions Amines Amino acids Carboxylic acids Catalysis Catalysts Chemical reactions Click chemistry Cysteamine Cysteine Heterogeneous catalysis Mesoporous materials
Title	Facile Synthesis of Cooperative Acid-Base Catalysts by Clicking Cysteine and Cysteamine on an Ethylene-Bridged Periodic Mesoporous Organosilica
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