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

被引:23
作者
Eiygi, Or [1 ]
Vaisman, Anna [1 ]
Nechmad, Noy B. [1 ]
Baranov, Mark [1 ]
Lemcoff, N. Gabriel [1 ,2 ]
机构
[1] Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel
[2] Ben Gurion Univ Negev, Ilse Katz Inst Nanoscale Sci & Technol, IL-84105 Beer Sheva, Israel
来源
ACS CATALYSIS | 2020年 / 10卷 / 03期
基金
以色列科学基金会;
关键词
photocatalysis; olefin metathesis; photochemistry; 3D printing; phosphites; CATALYST; POLYMERIZATION; COMPOSITES; ACTIVATION; ACCESS;
D O I
10.1021/acscatal.9b05079
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
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.
引用
收藏
页码:2033 / 2038
页数:11
相关论文
共 47 条
[1]   Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes [J].
Bantreil, Xavier ;
Poater, Albert ;
Urbina-Blanco, Cesar A. ;
Bidal, Yannick D. ;
Falivene, Laura ;
Randall, Rebecca A. M. ;
Cavallo, Luigi ;
Slawin, Alexandra M. Z. ;
Cazin, Catherine S. J. .
ORGANOMETALLICS, 2012, 31 (21) :7415-7426
[2]   Mixed N-heterocyclic carbene/phosphite ruthenium complexes: towards a new generation of olefin metathesis catalysts [J].
Bantreil, Xavier ;
Schmid, Thibault E. ;
Randall, Rebecca A. M. ;
Slawin, Alexandra M. Z. ;
Cazin, Catherine S. J. .
CHEMICAL COMMUNICATIONS, 2010, 46 (38) :7115-7117
[3]   Photoactivation of Ruthenium Olefin Metathesis Initiators [J].
Ben-Asuly, Amos ;
Aharoni, Anna ;
Diesendruck, Charles E. ;
Vidavsky, Yuval ;
Goldberg, Israel ;
Straub, Bernd F. ;
Lemcoff, N. Gabriel .
ORGANOMETALLICS, 2009, 28 (16) :4652-4655
[4]   Direct access to site-specifically phosphorylated-lysine peptides from a solid-support [J].
Bertran-Vicente, Jordi ;
Schuemann, Michael ;
Schmieder, Peter ;
Krause, Eberhard ;
Hackenberger, Christian P. R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) :6839-6843
[5]   Additive manufacturing with stimuli-responsive materials [J].
Boydston, A. J. ;
Cao, B. ;
Nelson, A. ;
Ono, R. J. ;
Saha, A. ;
Schwartz, J. J. ;
Thrasher, C. J. .
JOURNAL OF MATERIALS CHEMISTRY A, 2018, 6 (42) :20621-20645
[6]   Highly Selective Olefin Metathesis with CAAC-Containing Ruthenium Benzylidenes [J].
Butilkov, Danielle ;
Frenklah, Alexander ;
Rozenberg, Illya ;
Kozuch, Sebastian ;
Lemcoff, N. Gabriel .
ACS CATALYSIS, 2017, 7 (11) :7634-7637
[7]   Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment [J].
Cambie, Dario ;
Bottecchia, Cecilia ;
Straathof, Natan J. W. ;
Hessel, Volker ;
Noel, Timothy .
CHEMICAL REVIEWS, 2016, 116 (17) :10276-10341
[8]   Controlled living ring-opening-metathesis polymerization by a fast-initiating ruthenium catalyst [J].
Choi, TL ;
Grubbs, RH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1743-1746
[9]   Continuous flow ring-closing metathesis, an environmentally-friendly route to 2,5-dihydro-1H-pyrrole-3-carboxylates [J].
Drop, Marcin ;
Bantreil, Xavier ;
Grychowska, Katarzyna ;
Mahoro, Gilbert Umuhire ;
Colacino, Evelina ;
Pawlowski, Maciej ;
Martinez, Jean ;
Subra, Gilles ;
Zajdel, Pawel ;
Lamaty, Frederic .
GREEN CHEMISTRY, 2017, 19 (07) :1647-1652
[10]   Photoactivation of Ruthenium Phosphite Complexes for Olefin Metathesis [J].
Eivgi, Or ;
Guidone, Stefano ;
Frenklah, Alexander ;
Kozuch, Sebastian ;
Goldberg, Israel ;
Lemcoff, N. Gabriel .
ACS CATALYSIS, 2018, 8 (07) :6413-6418