Functionalization at Will of Rim-Differentiated Pillar[5]arenes

Paul Demay-Drouhard; Ke Du; Kushal Samanta; Xintong Wan; Weiwei Yang; Rajavel Srinivasan; Andrew C.H. Sue; Han Zuilhof

doi:10.1021/acs.orglett.9b01123

Functionalization at Will of Rim-Differentiated Pillar[5]arenes

Paul Demay-Drouhard, Ke Du, Kushal Samanta, Xintong Wan, Weiwei Yang, Rajavel Srinivasan, Andrew C.H. Sue^*, Han Zuilhof^*

^*Corresponding author for this work

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

45 Citations (Scopus)

Abstract

The development of an efficient synthetic route toward rim-differentiated C ₅ -symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C ₅ -symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki-Miyaura coupling. Afterward, BBr ₃ demethylation activates another rim for similar functionalizations.

Original language	English
Pages (from-to)	3976-3980
Journal	Organic Letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01123
Publication status	Published - 19 Apr 2019

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https://edepot.wur.nl/477645Licence: CC BY-NC-ND

CCDC 1896019: Experimental Crystal Structure Determination
Demay-Drouhard, P. (Creator), Du, K. (Creator), Samanta, K. (Creator), Wan, X. (Creator), Yang, W. (Creator), Srinivasan, R. (Creator), Sue, A. C. H. (Creator) & Zuilhof, H. (Creator), 20 Mar 2019
DOI: 10.5517/ccdc.csd.cc21myxk
Dataset
CCDC 1896026: Experimental Crystal Structure Determination
Demay-Drouhard, P. (Creator), Du, K. (Creator), Samanta, K. (Creator), Wan, X. (Creator), Yang, W. (Creator), Srinivasan, R. (Creator), Sue, A. C. H. (Creator) & Zuilhof, H. (Creator), 7 Feb 2019
DOI: 10.5517/ccdc.csd.cc21mz4t
Dataset
CCDC 1896021: Experimental Crystal Structure Determination
Demay-Drouhard, P. (Creator), Du, K. (Creator), Samanta, K. (Creator), Wan, X. (Creator), Yang, W. (Creator), Srinivasan, R. (Creator), Sue, A. C. H. (Creator) & Zuilhof, H. (Creator), 20 Mar 2019
DOI: 10.5517/ccdc.csd.cc21myzm
Dataset

Cite this

@article{76da96748e724a3782cff56cc2eed4e4,

title = "Functionalization at Will of Rim-Differentiated Pillar[5]arenes",

abstract = " The development of an efficient synthetic route toward rim-differentiated C 5 -symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C 5 -symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki-Miyaura coupling. Afterward, BBr 3 demethylation activates another rim for similar functionalizations. ",

author = "Paul Demay-Drouhard and Ke Du and Kushal Samanta and Xintong Wan and Weiwei Yang and Rajavel Srinivasan and Sue, {Andrew C.H.} and Han Zuilhof",

year = "2019",

month = apr,

day = "19",

doi = "10.1021/acs.orglett.9b01123",

language = "English",

volume = "21",

pages = "3976--3980",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

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TY - JOUR

T1 - Functionalization at Will of Rim-Differentiated Pillar[5]arenes

AU - Demay-Drouhard, Paul

AU - Du, Ke

AU - Samanta, Kushal

AU - Wan, Xintong

AU - Yang, Weiwei

AU - Srinivasan, Rajavel

AU - Sue, Andrew C.H.

AU - Zuilhof, Han

PY - 2019/4/19

Y1 - 2019/4/19

N2 - The development of an efficient synthetic route toward rim-differentiated C 5 -symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C 5 -symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki-Miyaura coupling. Afterward, BBr 3 demethylation activates another rim for similar functionalizations.

AB - The development of an efficient synthetic route toward rim-differentiated C 5 -symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C 5 -symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki-Miyaura coupling. Afterward, BBr 3 demethylation activates another rim for similar functionalizations.

U2 - 10.1021/acs.orglett.9b01123

DO - 10.1021/acs.orglett.9b01123

M3 - Article

AN - SCOPUS:85065089970

SN - 1523-7060

VL - 21

SP - 3976

EP - 3980

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Functionalization at Will of Rim-Differentiated Pillar[5]arenes

Abstract

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Datasets

CCDC 1896019: Experimental Crystal Structure Determination

CCDC 1896026: Experimental Crystal Structure Determination

CCDC 1896021: Experimental Crystal Structure Determination

Cite this