Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Du, Ya; Pearson, Ryan M.; Lim, Chern-Hooi; Sartor, Steven M.; Ryan, Matthew D.; Yang, Haishen; Damrauer, Niels H.; Miyake, Garret M.

doi:10.1002/chem.201702926

Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Journal Article · Tue Jun 27 00:00:00 EDT 2017 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201702926· OSTI ID:1533143

Du, Ya ^[1]; Pearson, Ryan M. ^[2]; ^[2]; Sartor, Steven M. ^[2]; Ryan, Matthew D. ^[2]; Yang, Haishen ^[3]; Damrauer, Niels H. ^[2]; ^[2]

Univ. of Colorado, Boulder, CO (United States); DOE/OSTI
Univ. of Colorado, Boulder, CO (United States)
Univ. of Colorado, Boulder, CO (United States); Shanghai University of Electric Power (China)

Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible-light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible-light PCs for trifluoromethylation reactions and dual photoredox/nickel-catalyzed C-N and C-S cross-coupling reactions, both of which have been historically exclusive to precious metal PCs.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Colorado, Boulder, CO (United States)

Sponsoring Organization:: USDOE Advanced Research Projects Agency - Energy (ARPA-E)

Grant/Contract Number:: AR0000683

OSTI ID:: 1533143

Alternate ID(s):: OSTI ID: 1375468

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 46 Vol. 23; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Photoinduced metal-free atom transfer radical polymerizations: state-of-the-art, mechanistic aspects and applications Yilmaz, Gorkem; Yagci, Yusuf Polymer Chemistry, Vol. 9, Issue 14 https://doi.org/10.1039/c8py00207j	journal	January 2018
Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones Berger, Anna Lucia; Donabauer, Karsten; König, Burkhard Chemical Science, Vol. 9, Issue 36 https://doi.org/10.1039/c8sc02038h	journal	January 2018
Single-molecule photoredox catalysis Haimerl, Josef; Ghosh, Indrajit; König, Burkhard Chemical Science, Vol. 10, Issue 3 https://doi.org/10.1039/c8sc03860k	journal	January 2019
Practical heterogeneous photoredox/nickel dual catalysis for C–N and C–O coupling reactions Liu, Yi-Yin; Liang, Dong; Lu, Liang-Qiu Chemical Communications, Vol. 55, Issue 33 https://doi.org/10.1039/c9cc00987f	journal	January 2019
Visible light promoted fluoroalkylation of alkenes and alkynes using 2-bromophenol as a catalyst Zhu, Erlin; Liu, Xiao-Xiao; Wang, An-Jun Chemical Communications, Vol. 55, Issue 81 https://doi.org/10.1039/c9cc06587c	journal	January 2019
A general and green fluoroalkylation reaction promoted via noncovalent interactions between acetone and fluoroalkyl iodides Mao, Ting; Ma, Ming-Jian; Zhao, Liang Chemical Communications, Vol. 56, Issue 12 https://doi.org/10.1039/c9cc09517a	journal	January 2020
Small-molecule activation with iron porphyrins using electrons, photons and protons: some recent advances and future strategies Anxolabéhère-Mallart, Elodie; Bonin, Julien; Fave, Claire Dalton Transactions, Vol. 48, Issue 18 https://doi.org/10.1039/c9dt00136k	journal	January 2019
Organocatalytic C–H fluoroalkylation of commodity polymers Lewis, Sally E.; Wilhelmy, Bradley E.; Leibfarth, Frank A. Polymer Chemistry, Vol. 11, Issue 30 https://doi.org/10.1039/c9py01884k	journal	January 2020
Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light Lemir, Ignacio D.; Castro-Godoy, Willber D.; Heredia, Adrián A. RSC Advances, Vol. 9, Issue 39 https://doi.org/10.1039/c9ra03642c	journal	January 2019
Reactivity control of a photocatalytic system by changing the light intensity Kerzig, Christoph; Wenger, Oliver S. Chemical Science, Vol. 10, Issue 48 https://doi.org/10.1039/c9sc04584h	journal	January 2019
Photocatalytic formation of carbon–sulfur bonds Wimmer, Alexander; König, Burkhard Beilstein Journal of Organic Chemistry, Vol. 14 https://doi.org/10.3762/bjoc.14.4	journal	January 2018
Photocatalytic Synthesis of Polycyclic Indolones Saget, Tanguy; König, Burkhard Universität Regensburg https://doi.org/10.5283/epub.43127	text	January 2020
Reactivity control of a photocatalytic system by changing the light intensity Kerzig, Christoph; Wenger, Oliver S. Royal Society of Chemistry https://doi.org/10.5451/unibas-ep73729	text	January 2019

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