Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs

The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐ (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11‐heptadecafluoroundecyl)silyl [C8F17(CH2)nSi(i‐Pr)2, where n=2 or 3], of the standard triisopropylsilyl (TIPS) group...

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Published in:	Advanced synthesis & catalysis Vol. 351; no. 7‐8; pp. 1035 - 1040
Main Authors:	Sancho, Amador Garcia, Wang, Xiao, Sui, Bin, Curran, Dennis P.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY‐VCH Verlag 01-05-2009
Subjects:	fluorous chemistry protecting groups relative reactivity triisopropylsilyl group
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Abstract	The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐ (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11‐heptadecafluoroundecyl)silyl [C8F17(CH2)nSi(i‐Pr)2, where n=2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride.
AbstractList	The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silyl and diisopropyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadeca-fluoroundecyl)silyl [C(8)F(17)(CH(2))(n)Si(i-Pr)(2), where n = 2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride. The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐ (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11‐heptadecafluoroundecyl)silyl [C8F17(CH2)nSi(i‐Pr)2, where n=2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride. magnified image The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐ (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11‐heptadecafluoroundecyl)silyl [C 8 F 17 (CH 2 ) n Si( i‐ Pr) 2 , where n =2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride. The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silyl and diisopropyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadeca-fluoroundecyl)silyl [C 8 F 17 (CH 2 ) n Si( i -Pr) 2 , where n = 2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride.
Author	Sancho, Amador Garcia Wang, Xiao Sui, Bin Curran, Dennis P.
AuthorAffiliation	1 Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Fax: (+1)-412-624-9861
AuthorAffiliation_xml	– name: 1 Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Fax: (+1)-412-624-9861
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CitedBy_id	crossref_primary_10_1016_j_tet_2013_01_017 crossref_primary_10_1080_00397911_2012_717241 crossref_primary_10_1002_ejoc_201700013 crossref_primary_10_1016_j_bmc_2014_04_063 crossref_primary_10_1021_cc100128w crossref_primary_10_1002_ejoc_201700195 crossref_primary_10_1021_jo100115h
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Snippet	The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐... The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silyl and... magnified image The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10‐ heptadecafluorodecyl)silyl and diisopropyl‐... The relative stabilities of two fluorous analogs, diisopropyl (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10, 10-heptadecafluorodecyl)silyl and...
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SubjectTerms	fluorous chemistry protecting groups relative reactivity triisopropylsilyl group
Title	Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs
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