22 Photochemistry Papers from 2022
At HepatoChem™, we had another big year in 2022. Our best yet. We added new members to our team, moved into our new office and manufacturing facility, spruced up our website and shipped our new photoreactor the Lucent360™ around the globe. By our unofficial tally, our PhotoRedox™ Boxes were cited over 60+ times in the literature in 2022 alone including the first citation using the Lucent360™. With more on the way (that we know of). We added new fun posts to our blog and newsletter and launched even more wavelength options for our EvoluChem™ LEDs while lowering the prices. All while continuing to offer our PhotoRedox™ Boxes and accessories.
The year 2023 promises even bigger things and some new surprises (look for 2023 to be the year of UV). However, before we look ahead to 2023, it’s time to look back at the year that was for 2022 in photochemistry. We started this “little” exercise 2 years ago during lockdown with our list of our 20 favorite papers of 2020 and we followed up last year as well. Now, more than ever, we are certain that we missed many great papers from the past year as it is virtually impossible for anyone (non-graduate student division) to keep track of all the great papers that have been published. As we described in the past, these are our favorite 22 photocatalysis papers from 2022. This is not a list that attempts to find the best, or most viewed, or most famous 22 papers from the year. (We described our general criteria here.) Nor is this list ranked in any way other than the order that we found them. (Although, if you want to tweet out and claim that your paper was #1 on our list, we won’t stop you or argue). Instead, this is just a list of the 22 papers that we thought were the best, funniest, oddest, most interesting, or downright unexpected. Every year, we always try to make sure the list is limited to one entry per author, but we always mess that up as well.
As always, our list is inherently biased to things that are related to visible-light photocatalysis or things that we could use as test reactions for our photoboxes. Open-access articles or papers easily accessible are always likely to catch our attention. As are papers from users using our products. For the first time, we asked our users to submit their favorite papers of the year, and many of those suggestions are present in this list.
Stereochemical editing logic powered by the epimerization of unactivated tertiary stereocenters
Authors: Yu-An Zhang, Vignesh Palani, Alexander E. Seim, Yong Wang, Kathleen J. Wang, Alison E. Wendlandt
Ref: Science, 2022, (378), 383-390.
Comment: Ok so we lied, #1 is our favorite paper of the year. And it got a lot of press so we probably aren’t surprising anyone with this one either. After this though, ignore the order.
Ammonia synthesis by photocatalytic hydrogenation of a N2-derived molybdenum nitride
Authors: Sangmin Kim , Yoonsu Park , Junho Kim, Tyler P. Pabst and Paul J. Chirik
Ref: Nature Synthesis, 2022 (1) 297-303
Comment: In the realm of blue light can do anything, this paper is extending pushing that boundary with a fascinating photochemical synthesis of ammonia from H2 and N2.
Photoswitchable Nitrogen Superbases: Using Light for Reversible Carbon Dioxide Capture
Authors: Lukas F. B. Wilm, Mowpriya Das, Daniel Janssen-Müller, Christian Mück-Lichtenfeld, Frank Glorius, and Fabian Dielmann
Ref: Angew.Chem. Int. Ed. 2022, 61, e202112344
Comment: Shine light, capture CO2 and form a stable complex. Change wavelength, release CO2. We can’t imagine any uses for this…
Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes
Authors: Dan E. Wise, Emma S. Gogarnoiu, Alana D. Duke, Joshua M. Paolillo, Taylor L. Vacala, Waseem A. Hussain, and Marvin Parasram
Ref: J. Am. Chem. Soc. 2022, 144, 34, 15437–15442
Comment: A photocatalytic anerobic cleavage of an alkenes to a carbonyl without an oxidant that lets many oxidatively sensitive functional groups survive.
Light-Driven Cobalt Hydride Catalyzed Hydroarylation of Styrenes
Authors: Enrico Bergamaschi, Victor J. Mayerhofer, and Christopher J. Teskey
Ref: ACS Catal. 2022, 12, 14806−14811
An EvoluChem user with a very cool Cobalt catalyzed method for making diarylalkane and triarylalkanes.
Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer
Authors: Roman Kleinmans, Tobias Pinkert, Subhabrata Dutta, Tiffany O. Paulisch, Hyeyun Keum, Constantin G. Daniliuc and Frank Glorius
Ref: Nature 605 477-482 (2022)
Comment: We could have selected any of a number of Glorius Group papers from the past year, but we’ll go with the Nature paper.
A general arene C–H functionalization strategy via electron donor–acceptor complex photoactivation
Authors: Abhishek Dewanji, Leendert van Dalsen, James A. Rossi-Ashton, Eloise Gasson, Giacomo E. M. Crisenza & David J. Procter
Ref: Nat. Chem. 2022 ASAP
Comment: A recent photocatalytic method for arene functionalization from the Procter group in Manchester.
Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C–C bonds
Authors: Yiman Gao, Jie Liu, Cong Wei,Yan Li, Kui Zhang, Liangliang Song and Lingchao Cai
Ref: Nature Communications (2022) 13:7450
Comment: Single-electron transfer method for constructing C-C bonds.
A Desaturative Approach for Aromatic Aldehyde Synthesis via Synergistic Enamine, Photoredox and Cobalt Triple Catalysis
Authors: Huaibo Zhao, Henry P. Caldora, Oliver Turner, James J. Douglas, and Daniele Leonori
Ref: Angew. Chem. Int. Ed. 2022, e202201870
Comment: A very cool methodology paper with a cameo at the end with a last minute Lucent360 reaction.
Bridging Plastic Recycling and Organic Catalysis: Photocatalytic Deconstruction of Polystyrene via a C–H Oxidation Pathway
Authors: Tengfei Li, Arjun Vijeta, Carla Casadevall, Alexander S. Gentleman, Tijmen Euser, and Erwin Reisner
Ref: ACS Catal. 2022, 12, 14, 8155–8163
Comment: We wrote about this one earlier in the year in our blog. A common theme from 2022 is papers using photochemistry to degrade polymers. We look forward to what’s next in this fascinating field.
Metallaphotoredox Decarboxylative Arylation of Natural Amino Acids via an Elusive Mechanistic Pathway
Authors: Manivel Pitchai, Antonio Ramirez, Don M. Mayder, Sankar Ulaganathan, Hemantha Kumar, Darpandeep Aulakh, Anuradha Gupta, Arvind Mathur, James Kempson, Nicholas Meanwell, Zachary M. Hudson, and Martins S. Oderinde
Ref: ACS Catal. ASAP
Comment: This work showed up the last week of 2022 and will technically be “published” in 2023, but what is publishing anyway. A really nice look at an interesting mechanism.
Visible-Light-Mediated (sp3)Cα−H Functionalization of Ethers Enabled by Electron Donor−Acceptor Complex
Authors: Sourav Roy and Indranil Chatterjee
Ref: ACS Organic & Inorganic Au 2022 2 (4), 306-311
Comment: An interesting article from EvoluChem users in the Chatterjee group at the Indian Institute of Technology Ropar.
Palladium Hydride-Enabled Hydroalkenylation of Strained Molecules
Authors: Ziyan Zhang and Vladimir Gevorgyan
Ref: J. Am. Chem. Soc. 2022, 144, 45, 20875–20883
Comment: A nice photochemical method for making strained molecules.
Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate
Authors: Can Liu, Ni Shen and Rui Shang
Ref: Nature Communications (2022) 13:354
Comment: Interesting method using phosphinophenolate mediated radical chemistry.
Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials
Authors: Katie A. Rykaczewski, Marc R. Becker, Manasi J. Anantpur, Rosario C. Sausa, Eric C. Johnson, Joshua A. Orlicki, Eric J. Bukowski, Jesse J. Sabatini*, and Corinna S. Schindler
Ref: J. Am. Chem. Soc. 2022, 144, 41, 19089–19096
Comment: High impact paper with explosive possibilities!
Selective Cross-Ketonization of Carboxylic Acids Enabled by Metallaphotoredox Catalysis
Authors: Andrew Whyte and Tehshik P. Yoon
Ref: Angew. Chem. Int. Ed. 2022, 61, e202213739
Comment: C-C bond formation from two carboxylic acids.
Lignin-Supported Heterogeneous Photocatalyst for the Direct Generation of H2O2 from Seawater
Authors: Aswin Gopakumar, Peng Ren, Jianhong Chen, Bruno Vinicius Manzolli Rodrigues, H. Y. Vincent Ching, Aleksander Jaworski, Sabine Van Doorslaer, Anna Rokicińska, Piotr Kuśtrowski, Giovanni Barcaro, Susanna Monti, Adam Slabon, and Shoubhik Das
Ref: J. Am. Chem. Soc. 2022, 144, 6, 2603–2613
A fun one that we wrote about this year in our blog. Photocatalyst where the solvent is seawater.
A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids
Authors: Tiffany Q. Chen, P. Scott Pedersen, Nathan W. Dow, Remi Fayad, Cory E. Hauke, Michael C. Rosko, Evgeny O. Danilov, David C. Blakemore, Anne-Marie Dechert-Schmitt, Thomas Knauber, Felix N. Castellano, and David W. C. MacMillan
Ref: J. Am. Chem. Soc. 2022, 144, 8296−8305
Comment: Everything you ever wanted to know about decarboxylative halogenation.
Photochemical Organocatalytic Benzylation of Allylic C–H Bonds
Authors: Emilien Le Saux, Margherita Zanini, and Paolo Melchiorre
Ref: J. Am. Chem. Soc. 2022, 144, 3, 1113–1118
Comment: A cool organocatalytic method for benzylation.
Title: Triplet Photosensitized para-Hydrogen Induced Polarization
Authors: Emily E. Brown, Iuliia Mandzhieva, Patrick M. TomHon, Thomas Theis, and Felix N. Castellano
Ref: ACS Cent. Sci. 2022, 8, 1548−1556
Comment: A fascinating paper that we don’t really understand.
Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates
Authors: Michael J. Tilby, Damien F. Dewez, Loïc R. E. Pantaine, Adrian Hall, Carolina Martínez-Lamenca, and Michael C. Willis
Ref: ACS Catal. 2022, 12, 10, 6060–6067
Comment: Very cool reaction.
Porphyrins as Promising Photocatalysts for Red-Light-Induced Functionalizations of Biomolecules
Authors: Katarzyna Rybicka-Jasińska, Tomasz Wdowik, Klaudia Łuczak, Aleksandra J. Wierzba, Olga Drapała, and Dorota Gryko
Ref: ACS Org. Inorg. Au 2022, 2, 5, 422–426
Comment: If you show us a porphyrin and you shine a light on it, we’re going to read your paper.
Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles
Authors: Philip R. D. Murray, Isabelle Nathalie-Marie Leibler, Sandrine M. Hell, Eris Villalona, Abigail G. Doyle, and Robert R. Knowles
Ref: ACS Catal. 2022, 12, 21, 13732–13740
Comment: We haven’t had a Knowles paper on one of our lists yet and we really need to amend that based on the number of great papers from them that we’ve read. This one from the Doyle and Knowles groups is a pretty diverse way to make a bunch of heterocycles.
Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer
Authors: Kang-Jie Bian, Shih-Chieh Kao, David Nemoto Jr., Xiao-Wei Chen & Julian G. West
Ref: Nature Communications 2022 13: 7881
If you publish towards the end of the year, you have a better chance of making this list. We’ll end with the last article that we read in 2022 from Julian West and coworkers.
We touched on many of this year’s amazing special issue of Chemical Reviews on photochemistry in last year’s list as many were already published online at the time. A few of our other favorite reviews and perspectives from the past year among the many, many that are out there.
The promise and pitfalls of photocatalysis for organic synthesis
Authors: Timothy Noel and Eli Zysman-Colman
Ref: Chem Catalysis 2022 (2), Pages 468-476
Comment: A nice perspective from early in the year on the state of affairs of photocatalysis.
The Catalysis Laboratory at Merck: 20 Years of Catalyzing Innovation
Authors: Rebecca T. Ruck*, Neil A. Strotman, and Shane W. Krska
Ref: ACS catalysis ASAP
Comment: Published just in time at the end of 2022, a worthy tribute to the incredible work over 20 years of Merck Catalysis.
Metal Complexes for Catalytic and Photocatalytic Reactions in Living Cells and Organisms
Authors: Hugo Madec, Francisca Figueiredo, Kevin Cariou, Sylvain Roland, Matthieu Sollogoub, and Gilles Gasser
Ref: Chem. Sci. Advance Article
Comment: An interesting look at metal complexes and photocatalysis that work in living organisms.
Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing
Authors: Agustin Millet, Paul T. Cesana, Kassandra Sedillo, Matthew J. Bird, Gabriela S. Schlau-Cohen, Abigail G. Doyle, David W. C. MacMillan, and Gregory D. Scholes
Ref: Acc. Chem Res. ASAP
Comment: A review looking at the work of the Bio-Inspired Light- Escalated Chemistry (BioLEC) Energy Frontier Research Center (EFRC) collaboration.