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2022 Paper(s) of the Year

Every year, our group participates in a “Paper of the Year” competition, where we each nominate five papers and then duke it out in a multi-hour debate. Looking through hundreds of papers in a few weeks is a great exercise: it helps highlight both creativity and its absence, and points towards where the field’s focus might turn next.

My picks are very personal—how could they not be?—and also biased towards towards experimental chemistry, owing to what our group focuses on. So, don’t take this as any attempt towards creating an objective list.

All the papers I really liked are listed below, with my top five listed in bold:

• A lovely electrochemical cross-electrophile coupling (Sevov). Great scope and forms challenging bonds.
• Carbon deletion through photochemistry, converting quinolines to indoles (Levin). My favorite of the skeletal editing papers, with apologies to the others (1, 2, 3, 4, 5, 6, 7). Pick 1/5.
• High-throughput additive screening reveals a new role for phthalimide in Ni-catalyzed cross-couplings (MacMillan, Dreher).
• Turning aldehydes into metal carbenoids (Nagib); self-recommending.
• Epimerization at tertiary carbons for “stereochemical editing” (Wendlandt).
• Setting stereocenters with vinyl carbocations, somehow (Nelson, Houk).
• Expanding automated synthesis to Csp₃ centers with “TIDA boronates” (Burke). An approach with a real chance of revolutionizing how we approach organic synthesis. Pick 2/5.
• Some beautiful asymmetric catalysis to form S-chiral sulfinate esters (Tan).
• Two papers disclosing the use of photoexcited nitroarenes to perform “ozonolysis without ozone” (Parasram, Leonori).
• Enantioselective conversion of carboxylic acids into amino acids (Meggers, Chen).
• Catalytic olefin hydroalkoxylation, through a tri-catalytic system (Ohmiya). Reminds me a little of Kanai’s tri-catalytic aldehyde allylation; in both cases, it’s hard to believe so many catalysts play nicely together.
• Deoxygenative trifluoromethylation (MacMillan), a reaction which speaks for itself.
• Functional group-tolerant Kochi–Salamon [2+2] cycloaddition in water, catalyzed by copper sulfate (Burns). Bizarre, unbelievable, outstanding. Pick 3/5. (With apologies to the other 2+2 cycloaddition papers: 1, 2, 3, 4, 5, 6, 7.)
• Pd-catalyzed C–H hydroxylation (Yu). Addresses a lot of my misgivings about C–H activation: directed by carboxylic acids, silver-free, scalable, and uses aqueous H₂O₂ (perhaps the best oxidant possible, after air).
• Red-light-mediated C–N coupling, through Os photocatalysis (Rovis). Suppresses a lot of the annoying mass balance issues that plague conventional photoredox.
• A nice mechanistic study of an enantioselective C–N coupling reaction (Peters, Fu).
• Mechanistic study and an improved phosphetane catalyst for C–N coupling (Radosevich).
• Studying the factors that lead to hydroxyl versus chlorine radical transfer in non-heme Fe complexes (Goldberg, de Visser).
• Studying the mechanism of enantioselective enzymatic C–H amination (Yang Yang, Peng Liu). Surprisingly, radical rebound is enantiodetermining! I remember being puzzled by the mechanism of this reaction when it was first published; this is a very satisfying resolution. Cool isotope studies & ab initio molecular dynamics seal the deal. Pick 4/5.
• The latest on photochemistry of Ni oxidative-addition complexes (Hadt). Beautiful physical inorganic chemistry; a lot of the details are beyond me, but clearly important work.
• Mechanistic study of PCET-mediated olefin hydroamination (Knowles).
• A really beautiful metal-free hydroamination (Wang/Wang).
• The latest on cobaltacene-based PCET mediators (Peters). Big fan of this program.
• Using aryl nitriles as sensors for electric field strength (Boxer). Also a really cool program: I liked this preprint too.
• Studying cation–acetonitrile dynamics with 2D IR and isotope labelling (Tokmakoff). I've written about this before
• A very nice ¹³C KIE study of the Suzuki reaction, emphasizing the importance of monoligated Pd even when using PPh₃ (Vetticatt, Hirschi). And another cool ¹³C KIE study for Hirschi.
• The first enantioselective beta-alkoxy elimination I’ve seen! (Streuff)
• An interesting way to functionalize ketones, via phosphorus-mediated umpolung (Ball).
• Investigating a concentration-dependent KIE for protonolysis of (cod)PtMe₂ (Bowring).
• Biocatalytic N-heterocycle methylation, with unbelievable regioselectivity (Hammer). Hammer also published a really exciting styrene hydration paper, albeit technically in 2023.
• Bifunctional redox-active esters add to styrenes to make a variety of heterocycles. (Knowles/Doyle).
• A nice illustration of the importance of conformer sampling workflows (Neese, Bistoni). See also work from Laplaza/Corminboef, Peter Chen, and Grimme.
• The latest equivariant neural network potential, faster than their previous work (Kozinsky).
• Espaloma, a differential neural network forcefield from the OpenForcefield folks.
• Studying cycloaddition dynamics with neural network potentials (Young, Duarte).
• Studying dynamic control of kinetic product ratios in cyclopropylidine opening using ML-learned potentials (Carpenter).
• wB97X-3c, the latest “composite method” (Grimme). If the reported speed and accuracy are true “in the wild,” every computational chemist ought to use this method. Pick 5/5.