NDLI: Tetrahydropyranylation of alcohols and phenols catalyzed by a new multi-wall carbon nanotubes-bound tin(IV) porphyrin

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Tetrahydropyranylation of alcohols and phenols catalyzed by a new multi-wall carbon nanotubes-bound tin(IV) porphyrin

Content Provider	Springer Nature Link
Author	Falahati, Ali Mohammad Gharaati, Shadab Kargar, Hadi
Copyright Year	2017
Abstract	In the present study, tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) using tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$], and tetrakis(p-aminophenyl)porphyrinatotin(IV) tetrafluoroborate, [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$], supported on multi-wall carbon nanotubes as new catalytic systems is investigated. These new catalysts, [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$@MWCNT] and [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$@MWCNT], were characterized using elemental analysis, FT-IR spectroscopic techniques, scanning electron microscopy and diffuse reflectance UV–Vis spectroscopic methods. In these catalytic systems, an optimization on the amounts of catalysts and amount of DHP was done in the tetrahydropyranylation of alcohols and phenols with DHP and the best outcomes were received in the presence of 0.01 mmol (40 mg) of [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$@MWCNT] and [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$@MWCNT] with 2 mmol of DHP. Efficiency and reusability are two important features of these new heterogenized catalysts for tetrahydropyranylation of primary, secondary and tertiary alcohols as well as phenols at room temperature. These catalysts were recovered several times with no loss on their initial activity, which indicates their high reusability and stability.In the present study, tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) using tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$], and tetrakis(p-aminophenyl)porphyrinatotin(IV) tetrafluoroborate, [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$], supported on multi-wall carbon nanotubes as new catalytic systems is investigated. These new catalysts, [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$@MWCNT] and [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$@MWCNT], were characterized using elemental analysis, FT-IR spectroscopic techniques, scanning electron microscopy and diffuse reflectance UV–Vis spectroscopic methods. In these catalytic systems, an optimization on the amounts of catalysts and amount of DHP was done in the tetrahydropyranylation of alcohols and phenols with DHP and the best outcomes were received in the presence of 0.01 mmol (40 mg) of [Sn$^{IV}$(TNH$_{2}$PP)(OTf)$_{2}$@MWCNT] and [Sn$^{IV}$(TNH$_{2}$PP)(BF$_{4}$)$_{2}$@MWCNT] with 2 mmol of DHP. Efficiency and reusability are two important features of these new heterogenized catalysts for tetrahydropyranylation of primary, secondary and tertiary alcohols as well as phenols at room temperature. These catalysts were recovered several times with no loss on their initial activity, which indicates their high reusability and stability.
Starting Page	1169
Ending Page	1178
Page Count	10
File Format	PDF
ISSN	1735207X
Journal	Journal of the Iranian Chemical Society
Volume Number	14
Issue Number	6
e-ISSN	17352428
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	2017-02-09
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Supported catalysts Heterogeneous catalysis Analytical Chemistry Physical Chemistry Lewis acids Hydroxyl compounds Biochemistry Nanostructures Inorganic Chemistry Tetrahydropyranyl ether Organic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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