Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis

Or Eivgi; Anna Vaisman; Noy B. Nechmad; Mark Baranov; N. Gabriel Lemcoff

doi:10.1021/acscatal.9b05079

Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis

Or Eivgi, Anna Vaisman, Noy B. Nechmad, Mark Baranov, N. Gabriel Lemcoff

Department of Chemistry

Ben-Gurion University of the Negev

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

Abstract

Herein we report two ruthenium benzylidene complexes with benzylphosphite ligands for olefin metathesis. Unlike the previously reported benzylidene phosphite complexes, the benzylphosphite complexes adopt a cis-dichloro configuration making them latent at ambient temperatures. Irradiation with visible light (420 nm and blue LED) prompts activation of the complexes and induces catalysis of olefin metathesis reactions. One of the complexes, cis-Ru-1, was found to be especially suitable for 3D printing of multilayered polydicyclopentadiene structures with excellent spatial resolutions. Additionally, complex cis-Ru-2 was designed with a chromatic orthogonal "kill switch" based on the 2-nitrobenzyl chemistry, allowing the destruction of the catalyst upon exposure to UV-C light.

Original language	American English
Pages (from-to)	2033-2038
Number of pages	6
Journal	ACS Catalysis
Volume	10
Issue number	3
DOIs	https://doi.org/10.1021/acscatal.9b05079
State	Published - 7 Feb 2020

Keywords

3D printing
olefin metathesis
phosphites
photocatalysis
photochemistry

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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10.1021/acscatal.9b05079

Cite this

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title = "Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis",

abstract = "Herein we report two ruthenium benzylidene complexes with benzylphosphite ligands for olefin metathesis. Unlike the previously reported benzylidene phosphite complexes, the benzylphosphite complexes adopt a cis-dichloro configuration making them latent at ambient temperatures. Irradiation with visible light (420 nm and blue LED) prompts activation of the complexes and induces catalysis of olefin metathesis reactions. One of the complexes, cis-Ru-1, was found to be especially suitable for 3D printing of multilayered polydicyclopentadiene structures with excellent spatial resolutions. Additionally, complex cis-Ru-2 was designed with a chromatic orthogonal {"}kill switch{"} based on the 2-nitrobenzyl chemistry, allowing the destruction of the catalyst upon exposure to UV-C light.",

keywords = "3D printing, olefin metathesis, phosphites, photocatalysis, photochemistry",

author = "Or Eivgi and Anna Vaisman and Nechmad, {Noy B.} and Mark Baranov and Lemcoff, {N. Gabriel}",

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doi = "10.1021/acscatal.9b05079",

language = "American English",

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T1 - Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis

AU - Eivgi, Or

AU - Vaisman, Anna

AU - Nechmad, Noy B.

AU - Baranov, Mark

AU - Lemcoff, N. Gabriel

PY - 2020/2/7

Y1 - 2020/2/7

N2 - Herein we report two ruthenium benzylidene complexes with benzylphosphite ligands for olefin metathesis. Unlike the previously reported benzylidene phosphite complexes, the benzylphosphite complexes adopt a cis-dichloro configuration making them latent at ambient temperatures. Irradiation with visible light (420 nm and blue LED) prompts activation of the complexes and induces catalysis of olefin metathesis reactions. One of the complexes, cis-Ru-1, was found to be especially suitable for 3D printing of multilayered polydicyclopentadiene structures with excellent spatial resolutions. Additionally, complex cis-Ru-2 was designed with a chromatic orthogonal "kill switch" based on the 2-nitrobenzyl chemistry, allowing the destruction of the catalyst upon exposure to UV-C light.

AB - Herein we report two ruthenium benzylidene complexes with benzylphosphite ligands for olefin metathesis. Unlike the previously reported benzylidene phosphite complexes, the benzylphosphite complexes adopt a cis-dichloro configuration making them latent at ambient temperatures. Irradiation with visible light (420 nm and blue LED) prompts activation of the complexes and induces catalysis of olefin metathesis reactions. One of the complexes, cis-Ru-1, was found to be especially suitable for 3D printing of multilayered polydicyclopentadiene structures with excellent spatial resolutions. Additionally, complex cis-Ru-2 was designed with a chromatic orthogonal "kill switch" based on the 2-nitrobenzyl chemistry, allowing the destruction of the catalyst upon exposure to UV-C light.

KW - 3D printing

KW - olefin metathesis

KW - phosphites

KW - photocatalysis

KW - photochemistry

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DO - 10.1021/acscatal.9b05079

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JF - ACS Catalysis

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ER -

Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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