Photoinduced electron transfer cyclizations of aryl-linked phthalimides

Yong Jun Lee; Do Hwan Ahn; Kyoung Sub Lee; Ae Rhan Kim; Dong Jin Yoo; Michael Oelgemöller

doi:10.1016/j.tetlet.2011.07.069

Photoinduced electron transfer cyclizations of aryl-linked phthalimides

Yong Jun Lee
, Do Hwan Ahn
, Kyoung Sub Lee
, Ae Rhan Kim
, Dong Jin Yoo^*
, Michael Oelgemöller

^*Corresponding author for this work

Department of Biological Sciences

Research output: Contribution to journal › Journal article › peer-review

17 Scopus citations

Abstract

The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO ₂H/H-exchange) products. In contrast, ω-phthalimido-meta- phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6-48%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18-38% yield. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28% and 35%, respectively.

Original language	English
Pages (from-to)	5029-5031
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2011.07.069
State	Published - 2011.09.28

Keywords

Photochemistry
Photocyclization
Photodecarboxylation
Photoinduced electron transfer
Phthalimide

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Pharmacy & Pharmacology
Chemistry
Biological Sciences

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10.1016/j.tetlet.2011.07.069

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title = "Photoinduced electron transfer cyclizations of aryl-linked phthalimides",

abstract = "The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO 2H/H-exchange) products. In contrast, ω-phthalimido-meta- phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6-48\%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18-38\% yield. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28\% and 35\%, respectively.",

keywords = "Photochemistry, Photocyclization, Photodecarboxylation, Photoinduced electron transfer, Phthalimide",

author = "Lee, \{Yong Jun\} and Ahn, \{Do Hwan\} and Lee, \{Kyoung Sub\} and Kim, \{Ae Rhan\} and Yoo, \{Dong Jin\} and Michael Oelgem{\"o}ller",

year = "2011",

month = sep,

day = "28",

doi = "10.1016/j.tetlet.2011.07.069",

language = "English",

volume = "52",

pages = "5029--5031",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "39",

}

TY - JOUR

T1 - Photoinduced electron transfer cyclizations of aryl-linked phthalimides

AU - Lee, Yong Jun

AU - Ahn, Do Hwan

AU - Lee, Kyoung Sub

AU - Kim, Ae Rhan

AU - Yoo, Dong Jin

AU - Oelgemöller, Michael

PY - 2011/9/28

Y1 - 2011/9/28

N2 - The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO 2H/H-exchange) products. In contrast, ω-phthalimido-meta- phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6-48%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18-38% yield. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28% and 35%, respectively.

AB - The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO 2H/H-exchange) products. In contrast, ω-phthalimido-meta- phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6-48%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18-38% yield. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28% and 35%, respectively.

KW - Photochemistry

KW - Photocyclization

KW - Photodecarboxylation

KW - Photoinduced electron transfer

KW - Phthalimide

UR - https://www.scopus.com/pages/publications/80052168215

U2 - 10.1016/j.tetlet.2011.07.069

DO - 10.1016/j.tetlet.2011.07.069

M3 - Journal article

AN - SCOPUS:80052168215

SN - 0040-4039

VL - 52

SP - 5029

EP - 5031

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Photoinduced electron transfer cyclizations of aryl-linked phthalimides

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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