My Personal Top 10 Preprints of 2018

Alright, I’ve done the count-up to preprint #1,000 and the quantitative, metrics-based rankings for which preprints were the “best” on ChemRxiv — however, today it’s Saturday, I’m off work, and I’m taking off my ChemRxiv hat to write about my *personal* favorite preprints of the past year. Yes, this list is subjective, intentionally avoids overlap with the preprints I listed in the Medium post and is not based on what I necessarily thought were the biggest advances of the year (I did a whole podcast on that), but rather which preprints I enjoyed reading the most, inspired the most discussion, or brought a smile to my face for some other reason. It helps that they’re all legitimately excellent scientific contributions as well.

Without further stalling and hedging, here’s my favorite preprints of 2018:

1. Buchwald-Hartwig Amination Using Pd(I) Dimer Precatalysts Supported by Biaryl Phosphine Ligands

Screen Shot 2018-12-22 at 2.53.01 PM.png

by Alex Spokoyny & co-workers (published in Dalton Transactions)

The research in this paper not only centers on biaryl phosphines (low-key my favorite phosphines), but was carried out almost entirely by undergraduates. The complexes are interesting (love those M–M bonds), the chemistry is solid and the authors are off to a great start (provided we can convince them to pursue synthetic organometallic chemistry in the future).

 

2. High Aspect Ratio Nanotubes Assembled from Macrocyclic Iminium Salts

Screen Shot 2018-12-22 at 2.57.27 PM.png

by William Dichtel & co-workers (published in PNAS)

This paper is a legitimate reimagining of how one can prepare nanotubes — this paper is super humble about how it turned the entire state-of the art on its head, in my opinion. I really cannot wait to see what this method lets people accomplish in 2019.

 

3. Catalytic Alkyne Arylation Using Amines as Traceless Directing Groups

Screen Shot 2018-12-22 at 3.01.06 PM.png

by Vy Dong & co-workers (published in ACIE)

This is the most interesting multicomponent reaction since the Ugi reaction, in my humble opinion. You don’t have to agree on that, but you can’t deny that this traceless approach for arylating alkynes isn’t freaking awesome.

 

4. Engineered Biosynthesis of β-Alkyl Tryptophan Analogs

Screen Shot 2018-12-22 at 3.04.15 PM.png

by Frances Arnold & co-workers (published in ACIE)

I’ll be honest: this paper’s on the list because 1) it’s absolutely incredible chemistry and 2) I was pretty miffed that, despite winning the Nobel Prize, none of Frances’ papers made it to the official Top 10. So here’s one of the coolest biosyntheses of the year, and congratulations again Frances!

 

5. Isonitriles as Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy in Radical Additions

Screen Shot 2018-12-22 at 3.07.41 PM.png

by Igor Alabugin & co-workers (published in JACS)

This paper looks at some really fascinating molecules and really takes apart the electronic underpinnings of why they react the way they do. It’s an approach I really appreciate and love seeing in action here. Also, coincidentally, it was the first ChemRxiv preprint to get into JACS, so that’s heart-warming, too!

 

6. Reversing Conventional Site-Selectivity in C(sp3)-H Bond Activation

Screen Shot 2018-12-22 at 3.11.15 PM.png

by Jin-Quan You & co-workers

In my mind, C–H activation chemistry was born from this weird area where everyone though it was impossible until people just, you know, did it. I feel like that kept happening for about a decade — “you can’t do X with C–H activation… oh hold on, someone just published that in JACS,” rinse and repeat. So, now that we all understand pretty well that C–H bonds can indeed be activated (so well, in fact, that I’d argue that the term activation is becoming progressively more unnecessary by the day), I love papers that go back to what C–H activation chemistry does best: turning our expectations upside down. JQY do just that in this paper and in stunning form — the selectivity switch will be welcomed by a lot of synthetic groups and goes to show that there’s still plenty to do in this area, even if it’s now officially a mainstay. Also, as far as I can tell it hasn’t yet been published in a journal, so this would be great time to email the authors if you happen to be the editor for an organic/organometallic journal…

 

7. Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

Screen Shot 2018-12-22 at 3.16.23 PM.png

by Guangbin Dong, Dong Xing & co-workers

Having worked in this group, I know how tough a problem this is to solve, and GBD and Dong Xing did some great work. Ni(0), starting materials and water — that’s it, and you get C–C bonds formed in ways that get you some incredibly useful synthetic scaffolds. It’s just beautiful chemistry that worked out to be really simple, and that’s a combination that I can’t say no to!

 

8. Bioinspired Thiophosphorodichloridate Reagents for Chemoselective Histidine Bioconjugation

Screen Shot 2018-12-22 at 3.19.25 PM.png

by Chris Chang & co-workers

I won’t even pretend not to be a Chris Chang fanboy — I react to the announcement of one of his seminars nearby the same way my wife responds to finding out our town is a stop on a Taylor Swift tour. So when we got this gorgeous paper from his lab, I’ll admit it — I geeked out. This is one of the more straightforward ways to tag a protein and uses histidine to do it. If you’re looking to probe or enhance a protein’s function I strongly suggest you take a look at this paper, as it will be a great starting point for a whole battery of different chemistries.

 

9. Structural Basis for Selectivity in Flavin-Dependent Monooxygenase-Catalyzed Oxidative Dearomatization

Screen Shot 2018-12-22 at 3.24.02 PM.png

by Alison Narayan & co-workers

I still haven’t quite figured out how Alison & co manage to make every paper they write such a delight to read. This one provides a structural basis for substrate binding in TropB, which is super important — the reaction this enzyme carries out is really useful and understanding the nuts and bolts of how it binds substrates is the first step to bending it to our whims. This paper is well-written and informative from top to bottom, so I really encourage you to give it a look!

 

10. What is an Organic Substance?

Screen Shot 2018-12-22 at 3.27.11 PM.pngby Lee Silverberg

This paper legitimately caused me to have an existential crisis. I had just assumed that there was a known definition of what an organic compound is and that it was in perfect agreement with the one I always use. Turns out I was wrong about there being a definition, and there are a lot of different perspectives on what that definition should be. I don’t agree with everything in this paper, and that’s alright, but it’s on this list because it didn’t just get me thinking, it haunted me.

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