A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

Holly Jane Davis; Daniel Häussinger; Thomas R. Ward; Yasunori Okamoto

doi:10.1002/cctc.202000488

A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

Holly Jane Davis, Daniel Häussinger, Thomas R. Ward, Yasunori Okamoto

Creative Interdisciplinary Research Division

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

Abstract

Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]⁺ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H₂O₂ generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.

Original language	English
Pages (from-to)	4512-4516
Number of pages	5
Journal	ChemCatChem
Volume	12
Issue number	18
DOIs	https://doi.org/10.1002/cctc.202000488
Publication status	Published - 2020 Sep 17

Keywords

Biomimetic
Organometallic complex
Photocatalysis
Reaction-in-water
Selective-dehydrogenation

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1002/cctc.202000488

Fingerprint Dive into the research topics of 'A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex'. Together they form a unique fingerprint.

Cite this

@article{9fd16d4c15064ce7a1cc83c73b32ed2f,

title = "A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex",

abstract = "Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2{\textquoteright},3{\textquoteright}-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.",

keywords = "Biomimetic, Organometallic complex, Photocatalysis, Reaction-in-water, Selective-dehydrogenation",

author = "Davis, {Holly Jane} and Daniel H{\"a}ussinger and Ward, {Thomas R.} and Yasunori Okamoto",

note = "Funding Information: The authors acknowledge Dr. Alessandro Prescimone, Mr. Adriano d'Addio and Mr. Daniel Joss for their help with the X-ray crystal structure analysis and NMR measurements. TRW acknowledges continued support from the Swiss National Science Foundation (grant 200020_182046), the NCCR Molecular Systems Engineering. HJD thanks the Marie Sk?odowska-Curie H2020-MSCA-IF-2018 for a postdoctoral fellowship. YO thanks JST ACT?X (JPMJAX1913) and support from FRIS, Tohoku University.",

year = "2020",

month = sep,

day = "17",

doi = "10.1002/cctc.202000488",

language = "English",

volume = "12",

pages = "4512--4516",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "18",

}

TY - JOUR

T1 - A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

AU - Davis, Holly Jane

AU - Häussinger, Daniel

AU - Ward, Thomas R.

AU - Okamoto, Yasunori

N1 - Funding Information: The authors acknowledge Dr. Alessandro Prescimone, Mr. Adriano d'Addio and Mr. Daniel Joss for their help with the X-ray crystal structure analysis and NMR measurements. TRW acknowledges continued support from the Swiss National Science Foundation (grant 200020_182046), the NCCR Molecular Systems Engineering. HJD thanks the Marie Sk?odowska-Curie H2020-MSCA-IF-2018 for a postdoctoral fellowship. YO thanks JST ACT?X (JPMJAX1913) and support from FRIS, Tohoku University.

PY - 2020/9/17

Y1 - 2020/9/17

N2 - Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.

AB - Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.

KW - Biomimetic

KW - Organometallic complex

KW - Photocatalysis

KW - Reaction-in-water

KW - Selective-dehydrogenation

UR - http://www.scopus.com/inward/record.url?scp=85088298323&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85088298323&partnerID=8YFLogxK

U2 - 10.1002/cctc.202000488

DO - 10.1002/cctc.202000488

M3 - Article

AN - SCOPUS:85088298323

VL - 12

SP - 4512

EP - 4516

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 18

ER -