23 Papers from 2023
Happy New Year from HepatoChem. Every year around this time, we like to look back at the previous year, share a list of our favorite papers and look ahead to where things are headed next. 2023 was a big year for us at HepatoChem. We moved into a new lab space, shipped Lucent360™ photoreactors around the world and expanded our product line of LEDs. Our PhotoRedox boxes, by our unofficial tally, were cited more than 70+ times in the literature in 2023 alone and topping 200+ since launch. We took part in a great research project using the Lucent360™ published this year. Also, we added many new posts to our blog and newsletter on fun and obscure topics such as Fenton Boats, DNA sequencing and the Origin of Life. What does 2024 have in store for us? Expect a new PhotoReactor, more LED options, more publications using our products, and more blog posts and newsletters.
As for our favorite papers from 2023? Some like to make their year-end lists sometime around early December fully forgetting an entire month of the year. We would like to be fashionably late and send this out some time in the next year. If you see this before the end of January, we consider it a success. This will be our 4th list “highlighting” the photochemistry literature (previous lists can be found here, 2020, 2021, and 2022). We would specifically like to highlight “highlighting” as reviewing the sum of photochemistry literature from 2023 is virtually impossible. It’s a safe bet to say that more photochemistry papers were published last year than any previous year, and we don’t have time for that. As we described in the past, these are our favorite 23 photocatalysis papers from 2023. This is not a list that attempts to find the best, or most viewed, or most famous 23 papers from the year. Or rank them in any way. This is not generated by Chat GPT, these are simply our handpicked favorites. As always, if your paper is Open Access, we’re more likely to like it as well. We are certain that we have missed many great papers from the past year and hope that you, the reader, can help us out with any that we missed. Instead, this is just a list of the 23 papers that we thought were the best, funniest, oddest, most interesting, or downright unexpected. Since most people are just skipping past this past this description anyway or simply hitting “control+F” for their name anyway, we’ll just get to the list.
So, here we go. Keep reading for our favorite papers from 2023 and then send us your favorites on twitter (@EvoluChem) or at info@hepatochem.
Paper 1:
Carbon-to-nitrogen single-atom transmutation of azaarenes
Authors: Jisoo Woo, Colin Stein, Alec H. Christian & Mark D. Levin
Ref: Nature 623, 77–82 (2023)
Link: https://www.nature.com/articles/s41586-023-06613-4
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Comment: This one got a lot of press and we’ll add a small bit to it. Swapping out carbon and replacing it with a nitrogen in a ring? Yeah, our favorite paper of the year with a bonus version here. After this, everything else is unranked.
Paper 2:
Photo-RDRP for everyone: Smartphone light-induced oxygen-tolerant reversible deactivation radical polymerization
(Open Access)
Authors: Arman Moini Jazani, Caroline Rawls, Krzysztof Matyjaszewski
Ref: European Polymer Journal, ASAP, 2023
Link:https://www.sciencedirect.com/science/article/pii/S0014305723008145?via%3Dihub
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Comment: A fun and odd one that fits the spirit of our list. Photoinitiated reversible polymerization with the light from an iPhone.
Paper 3:
The Merger of Aryl Radical-Mediated Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Cross-Coupling-Type Functionalization of Alkyl Iodides
Authors: Lewis Caiger, Huaibo Zhao, Timothée Constantin, James J. Douglas, and Daniele Leonori
Ref: ACS Catal. 2023, 13, 4985-4991
Link: https://pubs.acs.org/doi/10.1021/acscatal.3c00571
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Comment: Nice work from the Leonori lab and AstraZeneca with a scaled-up reaction using the Lucent360™.
Paper 4:
Anaerobic Hydroxylation of C(sp3)-H Bonds Enabled by the Synergistic Nature of Photoexcited Nitroarenes
Authors: Joshua M. Paolillo, Alana D. Duke, Emma S. Gogarnoiu, Dan E. Wise, and Marvin Parasram
Ref: J. Am. Chem. Soc. 2023, 145, 2794-2799
Link: https://pubs.acs.org/doi/10.1021/jacs.2c13502
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Comment: We shared this one in a newsletter earlier this year. We’ll borrow the comment from then… “From time to time, we must explain to someone how and why our company is named HepatoChem? Our original and still on-going business is oxidizing drug compounds to make metabolites. So, when we see a paper that combines our two favorite things, hydroxylation and photochemistry, it’s going to make our list.”
Paper 5:
Enantioselective Intermolecular Radical Amidation and Amination of Benzylic C–H Bonds via Dual Copper and Photocatalysis
(Open Access)
Authors: Xuemeng Chen, Zhong Lian, and Søren Kramer
Ref: Angew. Chem. Int. Ed. 2023, e202217638
Link: https://doi.org/10.1002/anie.202217638
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Comment:
An EvoluChem user with an exciting paper using the PhotoRedox Box TC for subzero photochemistry.
Paper 6:
Rapid Biomolecular Trifluoromethylation Using Cationic Aromatic Sulfonate Esters as Visible-Light-Triggered Radical Photocages
Authors: Nicholas J. Kuehl and Michael T. Taylor
Ref: J. Am. Chem. Soc.2023, 145, 42, 22878–22884
Link: https://pubs.acs.org/doi/10.1021/jacs.3c08098
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Comment: Protein labeling in a PhotoRedox Box.
Paper 7:
Photo- and Metal-Mediated Deconstructive Approaches to Cyclic Aliphatic Amine Diversification
Authors: David M. Soro, Jose B. Roque, Jonas W. Rackl, Bohyun Park, Stefan Payer, Yuan Shi, J. Craig Ruble, Alexey L. Kaledin, Mu-Hyun Baik, Djamaladdin G. Musaev, and Richmond Sarpong
Ref: J. Am. Chem. Soc.2023, 145, 20, 11245–11257
Link: https://pubs.acs.org/doi/10.1021/jacs.3c01318
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Comment: Breaking things with photochemistry in order to make diverse products.
Paper 8:
High-Throughput Determination of Stern-Volmer Quenching Constants for Common Photocatalysts and Quenchers
(Open Access)
Authors: Rachel N. Motz, Alexandra C. Sun, Dan Lehnherr, and Serge Ruccolo
Ref: ACS Organic & Inorganic Au, 2023 Articles ASAP
Link: https://pubs.acs.org/doi/full/10.1021/acsorginorgau.3c00019
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Comment: Another paper that we highlighted earlier this year. Give a team a robot and a library of photocatalysts and quenchers and you can get a high-throughput method for Stern-Volmer studies and a ton of data. This paper seems destined to be cited about 7 million times as everyone’s reference of choice.
Paper 9:
Photocatalytic and Photoinduced Phosphonylation of Aryl Iodides: A Batch and Flow Study
Authors: Romain Lapierre, Thi Minh Thi Le, Bruno Schiavi, Damien Thevenet, Marc Bazin, Ryan Buzdygon, Philippe Jubault,* and Thomas Poisson*
Ref: Org. Process Res. Dev., 2023, ASAP
Link: https://pubs.acs.org/doi/10.1021/acs.oprd.2c00379
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Comment: We’re grateful to Professors Poisson and Jubault and coworkers for letting us play a small part in their study looking at the phosphonylation of aryl iodides. Check this out for a look at the Lucent360™ in action for scale up in batch and flow.
Paper 10:
Genetically Encoded Photocatalysis Enables Spatially Restricted Optochemical Modulation of Neurons in Live Mice
(Open Access)
Authors: Kaixing Zeng, Zhi-Han Jiao, Qin Jiang, Ru He, Yixin Zhang, Wei-Guang Li, Tian-Le Xu, and Yiyun Chen
Ref: ACS Cent. Sci. 2023 ASAP
Link: https://doi.org/10.1021/acscentsci.3c01351
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Comment: Genetically encoding photocatalysts enables photochemical labeling of neurons inside live mice. Kind of amazing.
Paper 11:
Copper-Mediated Dehydrogenative C(sp3)-H Borylation of Alkanes
(Open Access)
Authors: Ruocheng Sang, Wangyujing Han, Hanwen Zhang, Carla M. Saunders, Adam Noble, and Varinder K. Aggarwal
Ref: J. Am. Chem. Soc.2023, 145, 28, 15207–15217
Link: https://pubs.acs.org/doi/10.1021/jacs.3c02185
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Comment: This should be a very useful, low cost and versatile reaction.
Paper 12:
Sustainable methane utilization technology via photocatalytic halogenation with alkali halides
(Open Access)
Authors: Jun Ma, Can Zhu, Keke Mao, Wenbin Jiang, Jingxiang Low, Delong Duan, Huanxin Ju, Dong Liu, Kun Wang, Yijing Zang, Shuangming Chen, Hui Zhang, Zeming Qi, Ran Long, Zhi Liu, Li Song & Yujie Xiong
Ref: Nature Communications volume 14, Article number: 1410 (2023)
Link: https://www.nature.com/articles/s41467-023-36977-0
Tweet:
Comment: Photochemical modification of methane
Paper 13:
Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions
(Open Access)
Authors: Kenji Ota, Kazunori Nagao, Dai Hata, Haruki Sugiyama, Yasutomo Segawa, Ryosuke Tokunoh, Tomohiro Seki, Naoya Miyamoto, Yusuke Sasaki & Hirohisa Ohmiya
Ref: Nature Communications volume 14, Article number: 6856 (2023)
Link: https://www.nature.com/articles/s41467-023-42639-y
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Comment: Interesting photochemical method for the synthesis of oligionucleotides.
Paper 14:
The Cost of Quantum Yield
(Open Access)
Authors: Han Li, Cui Wang, Felix Glaser, Narayan Sinha, and Oliver S. Wenger
Ref: Org. Process Res. Dev.2023, 27, 7, 1411–1419
Link: https://pubs.acs.org/doi/10.1021/acs.oprd.3c00167
Tweet:
Comment: How much are you paying for your photons?
Paper 15:
Metal-Organic Bichromophore Lowers the Upconversion Excitation Power Threshold and Promotes UV Photoreactions
(Open Access)
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. 2023, 145, 20, 11402–11414
Link: https://pubs.acs.org/doi/full/10.1021/jacs.3c02609
Tweet:
Comment: Another paper we shared earlier this year. We recently added UV capabilities to the Lucent360 extending the instrument’s range from 254 nm to 808 nm. As a result, we’ve started looking more into reactions that can be run at more “traditional” photochemistry wavelengths in the UV but also have visible light companions. That reading led us here, a great example of upconversion of blue light into the UV region.
Paper 16:
Sustainable Wood-Based Iron Photocatalyst for Multiple Uses with Sunlight: Water Treatment and Radical Photopolymerization
(Open Access)
Authors: Xiaolin Guo, Xinpeng Zhao, Xiongfei Luo, Yulian Pang, Bing Tian, Shouxin Liu, Shujun Li, Jian Li, Bernd Strehmel, and Zhijun Chen
Ref: Angew. Chem. Int. Ed. 2023, e202301242
Link: https://doi.org/10.1002/anie.202301242
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Comment: One of the most fun papers of the year. Fenton Boats! We wrote about this earlier this year in our blog.
Paper 17:
Photoinduced Cobalt Catalysis for the Reductive Coupling of Pyridines and Dienes Enabled by Paired Single-Electron Transfer
(Open Access)
Authors: Jingyang Qin, Manuel Barday, Samikshan Jana, Nil Sanosa, Ignacio Funes-Ardoiz, and Christopher J. Teskey
Ref: Angew. Chem. Int. Ed. 2023, e202310639
Link:https://onlinelibrary.wiley.com/doi/10.1002/anie.202310639
Tweet:
Comment: An EvoluChem user with an interesting demonstration with the PhotoRedox Box Duo.
Paper 18:
In situ Generated Iridium Nanoparticles as Hydride Donors in Photoredox-Catalyzed Hydrogen Isotope Exchange Reactions with Deuterium and Tritium Gas
Authors: Henrik Kramp, Remo Weck, Dr. Martin Sandvoss, Dr. Anna Sib, Dr. Gabriel Mencia, Dr. Pier-Francesco Fazzini, Prof.”…Dr. Bruno Chaudret, Dr. Volker Derdau
Ref: Angew. Chem. Int. Ed. 2023, 62, e202308983
Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202308983
Tweet:
Comment: We wrote about this one back in September. Hot labeling with photocatalysis.
Paper 19:
Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group
(Open Access)
Authors: Florian Lind, Kirill Markelov and Armido Studer
Ref:Chem. Sci., 2023,14, 12615-12620
Link: https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc04975b
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Comment: A new protecting group, removed by visible light.
Paper 20:
Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization
Authors: David F. Fernández, María González-Esguevillas, Sebastian Keess, Felix Schäfer, Jens Mohr, Andre Shavnya, Thomas Knauber, David C. Blakemore, and David W. C. MacMillan
Ref: Org. Lett. 2023 ASAP
Link: https://doi.org/10.1021/acs.orglett.3c00994
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Comment: Rapid diversification of aliphatic cores with a variety of photochemical methods.
Paper 21:
A Photoredox Reaction for the Selective Modification of 5″‘Carboxycytosine in DNA
Authors: Benjamin J. Mortishire-Smith, Sidney M. Becker, Angela Simeone, Larry Melidis, and Shankar Balasubramanian
Ref: J. Am. Chem. Soc.2023, 145, 19, 10505–10511
Link: https://pubs.acs.org/doi/10.1021/jacs.2c12558
Tweet:
Comment: A photochemical method for sequencing DNA using a PhotoRedox Box.
Paper 22:
Iron-mediated modular decarboxylative cross-nucleophile coupling
Authors: Grace A. Lutovsky, Samuel N. Gockel, Mark W. Bundesmann, Scott W. Bagley, Tehshik P. Yoon
Ref: Chem. 2023, 9, 6 1610-1621
Link: https://doi.org/10.1016/j.chempr.2023.04.008
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Comment: Direct decarboxylation of building blocks with cheap iron catalysts.
Paper 23:
Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes
Authors: Keri A. Steiniger, Matthew C. Lamb, and Tristan H. Lambert
Ref: J. Am. Chem. Soc.2023, 145, 21, 11524–11529
Link: https://pubs.acs.org/doi/10.1021/jacs.3c03634
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Comment: Last but not least. Free amines as cross-coupling partners.
Reviews/Perspectives
And now a few of our favorite reviews from the year.
Review 1:
(Photoredox) Organocatalysis in the Emergence of Life: Discovery, Applications, and Molecular Evolution
Authors: Maximilian Bechtel, Marian Ebeling, Laura Huber, and Oliver Trapp
Ref: Accounts of Chemical Research2023,56,20,2801-2813
Link: 10.1021/acs.accounts.3c00396
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Comment: Searching for the origin of life with photochemistry. From our blog. Our favorite review of the year.
Review 2:
Mechanisms and Synthetic Strategies in Visible Light-Driven [2+2]-Heterocycloadditions
Authors: Pietro Franceschi, Dr. Sara Cuadros, Dr. Giulio Goti, Prof.”…Dr. Luca Dell’Amico
Ref: Angewandte Chemie Int. Ed. 2023, 62 (8), e202217210
Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202217210
Tweet:
Comment: Another paper that we found via our foray in UV chemistry. Here is a great look at the historical development of visible-light alternatives for [2+2] cycloadditions.
Review 3:
Photobiocatalytic Strategies for Organic Synthesis
Authors: Megan A. Emmanuel, Sophie G. Bender, Catherine Bilodeau, Jose M. Carceller, Jacob S. DeHovitz, Haigen Fu, Yi Liu, Bryce T. Nicholls, Yao Ouyang, Claire G. Page, Tianzhang Qiao, Felix C. Raps, Damien R. Sorigué, Shang-Zheng Sun, Joshua Turek-Herman, Yuxuan Ye, Ariadna Rivas-Souchet, Jingzhe Cao, and Todd K. Hyster
Ref: Chem. Rev. 2023, 123, 9, 5459–5520
Link: https://pubs.acs.org/doi/10.1021/acs.chemrev.2c00767
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Comment: A great summary of biological photochemistry methods for synthesis. Congrats to everyone in the Hyster lab, and I mean everyone in the lab, who contributed to this work.
Review 4:
Photocatalytic Late-Stage C-H Functionalization
Authors: Peter Bellotti, Huan-Ming Huang, Teresa Faber, and Frank Glorius
Ref: Acc. Chem Res. ASAP
Link: https://pubs.acs.org/doi/10.1021/acs.chemrev.2c00478
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Comment: Everything you ever wanted to know about photochemical methods for late stage modifications.
Review 5:
Photochemical Methods Applied to DNA Encoded Library (DEL) Synthesis
Authors: Bianca Matsuo, Albert Granados, Guillaume Levitre, and Gary A. Molander
Ref: Acc. Chem. Res.2023, 56, 3, 385–401
Link: https://doi.org/10.1021/acs.accounts.2c00778
Tweet:
Comment: A great resource for DNA encoded libraries from the leader in the field.
Review 6:
Recent Advances in Visible Light Induced Palladium Catalysis
Authors: Bianca Matsuo, Albert Granados, Guillaume Levitre, and Gary A. Molander
Ref: Angew. Chem. Int. Ed. 2023 ASAP
Link: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202311972
Tweet:
Comment: Shining light on palladium.
