A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function

Revannath L. Sutar; Efrat Levin; Danielle Butilkov; Israel Goldberg; Ofer Reany; N. Gabriel Lemcoff

doi:10.1002/anie.201508966

A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function

Revannath L. Sutar, Efrat Levin, Danielle Butilkov, Israel Goldberg, Ofer Reany, N. Gabriel Lemcoff

Chemistry discipline

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

Abstract

A sulfur-chelated photolatent ruthenium olefin metathesis catalyst has been equipped with supersilyl protecting groups on the N-heterocyclic carbene ligand. The silyl groups function as an irreversible chromatic kill switch, thus decomposing the catalyst when it is irradiated with 254 nm UV light. Therefore, different types of olefin metathesis reactions may be started by irradiation with 350 nm UV light and prevented by irradiation with shorter wavelengths. The possibility to induce and impede catalysis just by using light of different frequencies opens the pathway for stereolithographic applications and novel light-guided chemical sequences.

Original language	English
Pages (from-to)	764-767
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	2
DOIs	https://doi.org/10.1002/anie.201508966
State	Published - 11 Jan 2016

Bibliographical note

Funding Information:
The Israel Science Foundation and the Magnet Program of the Office of the Chief Scientist of the Ministry of Industry, Trade & Laboris are gratefully acknowledged for financial support.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

Keywords

N-heterocyclic carbenes
metathesis
photochemistry
polymerization
ruthenium

Access to Document

10.1002/anie.201508966

Cite this

@article{56c992df160048eb8c3bc168ac92e6fd,

title = "A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function",

abstract = "A sulfur-chelated photolatent ruthenium olefin metathesis catalyst has been equipped with supersilyl protecting groups on the N-heterocyclic carbene ligand. The silyl groups function as an irreversible chromatic kill switch, thus decomposing the catalyst when it is irradiated with 254 nm UV light. Therefore, different types of olefin metathesis reactions may be started by irradiation with 350 nm UV light and prevented by irradiation with shorter wavelengths. The possibility to induce and impede catalysis just by using light of different frequencies opens the pathway for stereolithographic applications and novel light-guided chemical sequences.",

keywords = "N-heterocyclic carbenes, metathesis, photochemistry, polymerization, ruthenium",

author = "Sutar, {Revannath L.} and Efrat Levin and Danielle Butilkov and Israel Goldberg and Ofer Reany and Lemcoff, {N. Gabriel}",

year = "2016",

month = jan,

day = "11",

doi = "10.1002/anie.201508966",

language = "אנגלית",

volume = "55",

pages = "764--767",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "2",

}

TY - JOUR

T1 - A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function

AU - Sutar, Revannath L.

AU - Levin, Efrat

AU - Butilkov, Danielle

AU - Goldberg, Israel

AU - Reany, Ofer

AU - Lemcoff, N. Gabriel

PY - 2016/1/11

Y1 - 2016/1/11

N2 - A sulfur-chelated photolatent ruthenium olefin metathesis catalyst has been equipped with supersilyl protecting groups on the N-heterocyclic carbene ligand. The silyl groups function as an irreversible chromatic kill switch, thus decomposing the catalyst when it is irradiated with 254 nm UV light. Therefore, different types of olefin metathesis reactions may be started by irradiation with 350 nm UV light and prevented by irradiation with shorter wavelengths. The possibility to induce and impede catalysis just by using light of different frequencies opens the pathway for stereolithographic applications and novel light-guided chemical sequences.

AB - A sulfur-chelated photolatent ruthenium olefin metathesis catalyst has been equipped with supersilyl protecting groups on the N-heterocyclic carbene ligand. The silyl groups function as an irreversible chromatic kill switch, thus decomposing the catalyst when it is irradiated with 254 nm UV light. Therefore, different types of olefin metathesis reactions may be started by irradiation with 350 nm UV light and prevented by irradiation with shorter wavelengths. The possibility to induce and impede catalysis just by using light of different frequencies opens the pathway for stereolithographic applications and novel light-guided chemical sequences.

KW - N-heterocyclic carbenes

KW - metathesis

KW - photochemistry

KW - polymerization

KW - ruthenium

UR - http://www.scopus.com/inward/record.url?scp=84958740770&partnerID=8YFLogxK

U2 - 10.1002/anie.201508966

DO - 10.1002/anie.201508966

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 26586469

AN - SCOPUS:84958740770

SN - 1433-7851

VL - 55

SP - 764

EP - 767

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 2

ER -

A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this