» Articles » PMID: 28654171

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

Overview
Journal Chemistry
Specialty Chemistry
Date 2017 Jun 28
PMID 28654171
Citations 54
Authors
Affiliations
Soon will be listed here.
Abstract

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.

Citing Articles

New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp)-F Bond Cleavage.

Roy S, Besset T JACS Au. 2025; 5(2):466-485.

PMID: 40017776 PMC: 11862972. DOI: 10.1021/jacsau.4c01158.


Ultrafast photophysics of -substituted 2,5-bis(arylethynyl) rhodacyclopentadienes: thermally activated intersystem crossing.

Guo Z, Wang Y, Heitmuller J, Sieck C, Prufer A, Ralle P Chem Sci. 2024; .

PMID: 39176244 PMC: 11337014. DOI: 10.1039/d4sc04306e.


Photocatalytic systems: reactions, mechanism, and applications.

Mohamadpour F, Amani A RSC Adv. 2024; 14(29):20609-20645.

PMID: 38952944 PMC: 11215501. DOI: 10.1039/d4ra03259d.


Mechanistic investigations of polyaza[7]helicene in photoredox and energy transfer catalysis.

Rocker J, Zahringer T, Schmitz M, Opatz T, Kerzig C Beilstein J Org Chem. 2024; 20:1236-1245.

PMID: 38887585 PMC: 11181280. DOI: 10.3762/bjoc.20.106.


Impact of Alkyl Core Substitution Kinetics in Diaryl Dihydrophenazine Photoredox Catalysts on Properties and Performance in O-ATRP.

Puffer K, Corbin D, Miyake G ACS Catal. 2024; 13(21):14042-14051.

PMID: 38883439 PMC: 11178316. DOI: 10.1021/acscatal.3c04060.


References
1.
Resch-Genger U, Grabolle M, Cavaliere-Jaricot S, Nitschke R, Nann T . Quantum dots versus organic dyes as fluorescent labels. Nat Methods. 2008; 5(9):763-75. DOI: 10.1038/nmeth.1248. View

2.
Noble A, McCarver S, MacMillan D . Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides. J Am Chem Soc. 2014; 137(2):624-7. PMC: 4308738. DOI: 10.1021/ja511913h. View

3.
Treat N, Sprafke H, Kramer J, Clark P, Barton B, Read de Alaniz J . Metal-free atom transfer radical polymerization. J Am Chem Soc. 2014; 136(45):16096-101. DOI: 10.1021/ja510389m. View

4.
Schultz D, Yoon T . Solar synthesis: prospects in visible light photocatalysis. Science. 2014; 343(6174):1239176. PMC: 4547527. DOI: 10.1126/science.1239176. View

5.
Hari D, Konig B . Synthetic applications of eosin Y in photoredox catalysis. Chem Commun (Camb). 2014; 50(51):6688-99. DOI: 10.1039/c4cc00751d. View