Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

Jie Han; Xisen Hou; Chenfeng Ke; Huacheng Zhang; Nathan L. Strutt; Charlotte L. Stern; J. Fraser Stoddart

doi:10.1021/acs.orglett.5b01418

Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

Jie Han, Xisen Hou, Chenfeng Ke, Huacheng Zhang, Nathan L. Strutt, Charlotte L. Stern, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

32 Scopus citations

Abstract

A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control, affording the desired oligo-substituted pillar[5]arene derivatives. In addition, the regioisomers of these derivatives can be isolated by installing triflate groups on the free hydroxyl groups. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	3260-3263
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.5b01418
State	Published - Jul 2 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5b01418

Cite this

@article{021839787abf407faaf569969aed370a,

title = "Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives",

abstract = "A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control, affording the desired oligo-substituted pillar[5]arene derivatives. In addition, the regioisomers of these derivatives can be isolated by installing triflate groups on the free hydroxyl groups. (Chemical Equation Presented).",

author = "Jie Han and Xisen Hou and Chenfeng Ke and Huacheng Zhang and Strutt, {Nathan L.} and Stern, {Charlotte L.} and Stoddart, {J. Fraser}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jul,

day = "2",

doi = "10.1021/acs.orglett.5b01418",

language = "English (US)",

volume = "17",

pages = "3260--3263",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

AU - Han, Jie

AU - Hou, Xisen

AU - Ke, Chenfeng

AU - Zhang, Huacheng

AU - Strutt, Nathan L.

AU - Stern, Charlotte L.

AU - Stoddart, J. Fraser

PY - 2015/7/2

Y1 - 2015/7/2

N2 - A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control, affording the desired oligo-substituted pillar[5]arene derivatives. In addition, the regioisomers of these derivatives can be isolated by installing triflate groups on the free hydroxyl groups. (Chemical Equation Presented).

AB - A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control, affording the desired oligo-substituted pillar[5]arene derivatives. In addition, the regioisomers of these derivatives can be isolated by installing triflate groups on the free hydroxyl groups. (Chemical Equation Presented).

UR - http://www.scopus.com/inward/record.url?scp=84935049339&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84935049339&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b01418

DO - 10.1021/acs.orglett.5b01418

M3 - Article

C2 - 26083303

AN - SCOPUS:84935049339

SN - 1523-7060

VL - 17

SP - 3260

EP - 3263

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1051111: Experimental Crystal Structure Determination

CCDC 1051134: Experimental Crystal Structure Determination

CCDC 1051137: Experimental Crystal Structure Determination

Cite this

Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1051111: Experimental Crystal Structure Determination

CCDC 1051134: Experimental Crystal Structure Determination

CCDC 1051137: Experimental Crystal Structure Determination

Cite this