Low energy light-triggered oxidative cleavage of olefins

Rajesh S. Murthy; Moses Bio; Youngjae You

doi:10.1016/j.tetlet.2008.12.069

Low energy light-triggered oxidative cleavage of olefins

Rajesh S. Murthy
, Moses Bio
, Youngjae You

Pharmaceutical Sciences

South Dakota State University

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

69 Scopus citations

Abstract

A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygen-mediated cleavable linker. Low intensity light of 200 mW/cm² was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.

Original language	English
Pages (from-to)	1041-1044
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.069
State	Published - Mar 4 2009

Keywords

Dioxetane
Olefin
Photocleavage
Singlet oxygen

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10.1016/j.tetlet.2008.12.069

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title = "Low energy light-triggered oxidative cleavage of olefins",

abstract = "A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygen-mediated cleavable linker. Low intensity light of 200 mW/cm2 was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80\% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.",

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author = "Murthy, \{Rajesh S.\} and Moses Bio and Youngjae You",

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T1 - Low energy light-triggered oxidative cleavage of olefins

AU - Murthy, Rajesh S.

AU - Bio, Moses

AU - You, Youngjae

PY - 2009/3/4

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N2 - A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygen-mediated cleavable linker. Low intensity light of 200 mW/cm2 was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.

AB - A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygen-mediated cleavable linker. Low intensity light of 200 mW/cm2 was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.

KW - Dioxetane

KW - Olefin

KW - Photocleavage

KW - Singlet oxygen

UR - https://www.scopus.com/pages/publications/58149494193

U2 - 10.1016/j.tetlet.2008.12.069

DO - 10.1016/j.tetlet.2008.12.069

M3 - Article

AN - SCOPUS:58149494193

SN - 0040-4039

VL - 50

SP - 1041

EP - 1044

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Low energy light-triggered oxidative cleavage of olefins

Abstract

Keywords

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