Andrei Yudin
@andrei_yudin
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Prof at U Toronto. Associate Editor for @ChemicalScience . Trying to understand the universe.
Toronto, Ontario
Joined July 2009
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Memorable night with Phil
@Dawson_Group
and Barry Sharpless in Del Mar earlier today. As usual: dinner turning into a marathon chemistry discussion. Thank you Phil and Barry!
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Left it on the grill for 3 hours… I think this is now graphene. The whole thing weighs about 2 grams.
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As you shut down your labs try to set up a few crystallizations and just leave the bastards. Some particularly uncooperative macrocyles or what not. Who knows. You may smile at this suggestion some months from now.
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I can't contain my excitement about the scholarly work that is about to appear in our journal. I applaud the authors for their painstaking perusal of chemistry lit and correcting the ghastly Times/unbalanced structure eyesores. Their abstract says it all.
@ChemicalScience
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Dichloromethane is the most overrated solvent anyway. Should not be used with amines in particular.
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If I started in new lab now (as grad student or pdf) I would not do any experiments for 2 weeks. Instead I’d go and read ALL papers and theses my new lab has produced (if it is a new PI lab - all of their previous papers). There is nothing more empowering and consequential.
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To students writing papers with their advisors. Strategy A in infinitely better than B:
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When all is said and done it will be a molecule that will stop this virus.
We’ll stare at its structure, imagine how its bonds spin, and lament at why it took so long. It will be a moon landing sort of moment. Some people will get tattoos of that structure, I am telling you.
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Someone asked me: is it important to read older literature (60s, 70s, 80s,...)? Isn’t it long outdated?
You mean the golden age when people did fearless blue sky investigations and financial troubles did not force them to write grants on stuff they weren’t keen on? I think so.
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I am going to place a thought-provoking piece on ChemRxiv that contains a rigorous proof for why diversity of backgrounds (gender, ethnic, etc) is essential in science. Some of it might surprise you, but it is entirely apolitical. The arguments are bullet-proof and logical.
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It is comforting that this virus does not spread sideways:
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I thought I have seen many things during this trip to Germany. But nothing prepared me for Cl13(-) anion by Riedel and co-workers. Yes, 13 chlorine atoms…
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In this paper we explore the dark conformational space.
Using ‘dominant rotors’ we show how unusual conformations can be stabilized in macrocycles.
Huge thanks to the team, especially
@DiegoBenDiaz
, who led the project.
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I see this nonsense in pretty much every chemistry textbook. A covalent bond between H and Br... Especially mind-blowing in a dipolar aprotic solvent.
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I am sitting at our lab problem set. Students refer to (COCl)2, or oxalyl chloride, as “cockl”. I have not heard this colloquialism before…
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When my wife gets home from her long shift, goes on to dictate and make endless phone calls regarding patients, I have second thoughts about the significance of my own contributions to this society. Her resilience and mental capacity are exceptional.
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A good guide for students on how to avoid such ghastly drawings.
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One of the best remarks I have ever got from a student was when one of my very first undergrads ran a reaction in open flask despite me telling him that the reaction “needs nitrogen atmosphere”.
“There is 78% of nitrogen in air. I figured this might be enough”
It is logical.
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Super happy for my mentor Barry, I am pictured with him here in 2016. Will never forget how way back in early 2000’s he grabbed my backpack when I visited and said: “listen to this sound (while clicking and releasing the buckle)!” Congratulations to
@CarolynBertozzi
and Meldal!
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I once taught a carbohydrate lecture and students had trouble remembering which one was alpha and which was beta. So I created this "tool". Alpha legitimately points down. No student got confused about it ever since.
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Few people know it, but every single process chem paper gets sent to me for vetting. If I get good yield, it is legit, decent stuff. They put my initials next to the yield I got. Often in green. I never insist on co-authorship b/c I am good that way.
@DrLCsquare
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I am very grateful for this award and to
@peterseeberger
in particular for support. Looking forward to using this
@AvHStiftung
opportunity for my sabbatical in his lab in Berlin (well, throughout all of Germany, I suppose!) July 1 - December 31 of this year.
He is strengthening scientific and cultural relations between Canada and Germany 🇨🇦🇩🇪: The chemist
@andrei_yudin
is to receive the Konrad Adenauer Research Award.
@UofT
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It says “Because Patients are Waiting” below the logo. Waiting for what? For 5-valent carbon?
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As opposed to science, art’s main objective is irreproducibility.
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@ChemicalScience
symposium underway. Thx
@dmac68
for a great kick-off talk. Looking forward to posters and other lectures. Fun organizing the scientific part w/
@Melchiorre_P
and Ning Jiao.
@aicooper
and
@MayCopsey
thx for bringing us here!
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My own "yes, but" logic for 3rd year organic chemistry students - just to keep people on edge.
@_yesbut_
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Sincere congrats to my colleague
@RousseauxGroup
who has been promoted to Associate Professor!
I have learned a lot of cool science from Sophie and it is just fabulous to have her on our faculty. She is a superb mentor and a great teacher who thinks deeply.
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Happy 80th birthday to my mentor Barry Sharpless! Thank you for sharing your penetrating insights over the years. We re not planning anything yet by way of a large gathering, but I am looking forward to a dinner in the Fall with M. G. Finn and
@Dawson_Group
. Here we are in 2016:
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There are wonderful lessons we learned with the lab of
@Honggen_W
at Sun Yat-Sen University. Silicon effect has been known for a while, but here are some unanticipated features of carbon-boron bond and its role in organic chemistry
@J_A_C_S
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Ever since my PhD (largely on fluorine chemistry) I have tried to be mindful of the corrupting effect of 19F NMR on one’s mental health. It would look super clean, but then you would run 1H (which is always way worse) and that is when the reality would sink in…
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Woke up and thought it was all a bad dream. But no... I am 1/8th Ukrainian myself (father’s grandmother was from there) and I am feeling the pain of the innocent people.
С роднёй в Херсоне говорили. Они с трудом купили несколько литров воды и очень рады этой простой покупкe.
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A student asked me how to develop a solid knowledge of organic reactions.
There’s only one way: to run them. Memorization is useless. You really do not learn anything this way. But if you run them once - you’ll remember them forever.
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Not long ago, we initiated a program aimed at repurposing common reagents towards construction of unexplored functional groups. This paper takes on NaBH3CN, a common reducing agent. It was fun to collaborate with
@A_Aspuru_Guzik
and
@SeferosGroup
!
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Another reminder that structural biologists are not allowed to report chemical structures. Please seek professional help first. I made this slide several years ago and I am certain there are even better gems out there.
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Here we introduce the concept of a "structural pin," a hydrogen bond that predominantly dictates the conformation of a macrocycle. This discovery offers a tool for examining the dynamic behavior of macrocycles and optimizing their structures.
@angew_chem
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Sincere thanks to all the students past and present who enable research in academic labs.
Congratulations to Professors
@myrna_simpson
and
@andrei_yudin
on their Canada Research Chair appointments.
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I have a ton of controversial slides in my undergrad course to help (?) navigate the uneasy terrains of chemistry...
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With
@Sean_SJ_Huh
(our recent PhD!) and
@GeorgeJSaunders
we deployed the rarely used Cornforth rearrangement to remove an atom from a macrocycle. This
@angew_chem
paper studies the interplay between reactivity and uncommon conformational states.
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Application of strain release in traditional veterinary medicine:
...external wounds of cows are packed with crystalline iodine. Application of turpentine (rich in pinene) leads to exothermic eruption. It vaporizes iodine, allowing it to penetrate inaccessible areas of the wound.
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As I look back over the past 20 years of teaching, this test answer (in a class aimed at chem non-specialists) is still my favourite. The students were asked to REDUCE this molecule with NaBH4. The answer is not incorrect (but borohydride’s services are not retained)...
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Very happy to see this joint effort with
@GongChenLab
@J_A_C_S
. We both love rarely visited conformational space. Gong lab’s reaction implants a rigid aryl brace between Asp, His, and Asn residues, delivering stunning structural motifs.
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For me, cooking is the primary way of communicating with my mother. She’s had Alzheimer’s for the past 6 years. So we can’t really talk, but back in the day she was the most vivacious and outgoing person I have come across. Tastes and smells take me back. Here she is in 1982.
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R.I.P. Professor Rolf Huisgen.
I last saw him in Munich in 2016. Here we are, along with Prof. Steglich. We had a wonderful lunch and, at the end, Rolf told me to tighten my shoe laces because they were undone and it started to rain. He did it in a very fatherly way.
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As part of an effort in synthetic half-reactions we considered (with my terrific PhD student Tien) the merits of enthalpic “retooling” of existing processes. In this
@ChemicalScience
work we “connect” NO cleavage with epoxide formation several bonds away.
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Microwave ovens have made a successful transition from kitchen to lab, with all those wonderful microwave reactors we now use. But what about toasters? This powerful tech has totally gone under the radar, imho.
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A discussion yesterday reminded me of Dr. Thomas Laube, who visited the Olah lab the 90's with the intent to crystallize challenging carbocations. He published amazing single-author papers where hyperconjugative effects were "seen" for the first time.
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RIP Prof. Negishi. One of the defining moments in my formative years was his talk on double metal catalysis. It was intuitive and devoid of any complex arguments, but very powerful. I recall how he visited Loker Institute (bear in mind that he came from the H. C. Brown “camp”).
We mourn the passing of our colleague, friend, and mentor -- Professor Ei-ichi Negishi.
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I really want to thank all my lab members past and present! Had a lovely celebration and a trip down the memory lane.
I love you guys and hope you and your loved ones are safe.
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I was very sad to learn about the passing of Bob Grubbs. While I never worked for Bob, we had a great relationship. He offered invaluable advice on my lab’s first electrochemical papers and we shared interest in where rare metals were being mined around the world. RIP Bob.
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Happy 🇨🇦 day, everyone! This year is special for me in this wonderful country. I have lived in:
USSR/Russia 22 years
US 6 years
Canada 22 years
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For a Synlett
@thiemechemistry
account I am writing, I needed a reference to what people had to do before Weinreb amide. I mentioned this old H. C. Brown work in my talks (the “chemistry lore”), but only now managed to retrieve the reference. I find the comments interesting.
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Which structure is more stable?
To a chemist they are the same, of course. But someone trained in arts/design would vote for the first one. Flat base = feeling of stability. Diagonal view associates with movement.
#perception
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Together with my students Sean Huh and Solomon Appavoo, we evaluate the role of amidines on the conformation of cyclic peptides. It is a marvellous functionality: isosteric with amides, but way off in terms of pKa.
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Together with
@SchindlerLab
we have put together a themed collection on New Reactivity
@ChemicalScience
. It has been a fun project with Corinna! Take a look at this diverse collection of articles.
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Dr. Jovana Yudin after vaccination earlier today. Things are moving on the front lines!
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Tonight is kourma-shurpa. A rich and flavourful lamb soup popular in Uzbekistan (overall my favourite food is from that country). Uyghur people might also recognize this dish.
#chemistswhocook
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A special day at
@LMU_Muenchen
, full of insights from Prof. Herbert Mayr, one of my scientific heroes. Lovely to see the setup for measuring Nu/E parameters and revisit the enduring problem of orbital control in cycloadditions (remarkable finding):
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When I read a well-referenced process chemistry paper about some therapeutic agent I am reminded by how many people contribute to drug discovery.
Unbeknownst to them, mind you.
The unsung heroes who, in an obscure paper decades ago noted some odd solvent effect or what not.
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Here is my annual reminder that just because a molecule is completely unstable on silica gel does not mean it is synthetically useless.
An example: n-BuLi.
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Tien defended his excellent thesis today. I participated remotely from Berlin and now look forward to shaking his hand when an opportunity arises. Next stop for Tien is going to be the call of duty in Taiwan army. Looking forward to welcoming him back into science after that!
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I am very much looking forward to having Ryan Gilmour
@GilmourLab
join us as an Associate Editor
@ChemicalScience
. His expertise in a number of areas will be really valuable. Welcome Ryan!
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This is a surprising result suggesting that some well-known claims that metals template cyclizations might need to be reexamined. The experiments here point to the role of chloride (vs cation) in cyclization.
Chloride-Assisted Peptide Macrocyclization
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Whenever I think of Vic Snieckus, vitality is the first word that comes to mind.
Last time I heard from him was during our November CSC Organic Division meeting. He actively participated until the very end.
RIP, Vic. You will be missed.
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Congratulations to
@dmac68
@MacMillan_Lab
and
@ben_list
for the
@NobelPrize
. I have always felt that the idea that a nucleophile (amine) makes an electrophile (aldehyde) more (!) electrophilic was, at its core, an awesome way to drive catalysis. Great news!
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I want my students to get rid of some cliches in their writing:
- “Albeit” (too Shakespearian. It is 2019)
- “With catalyst X in hand...” (I am dying to know: was it your left hand?)
- “At the outset” (please, just don’t)
There are many others and they are like weeds...
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Industrial production of NaN3:
...liquid sodium amide (from Na and NH3) is converted to sodium azide by reaction with dinitrogen monoxide at approximately 230°C in a horizontal nickel reactor... the separated residual crystalline material (NaN3) is dried at 110°C... lovely prep
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With
@dixon_group
@RhPdCu
@VarinderAggar11
@EdAndersonGroup
and Ben Davis here in Bavaria
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The area of Berlin I now live in (for the next 6 months) is called Prenzlauer Berg. A very picturesque urban environment. Commuting daily to my new office at
@MpiciPotsdam
from there. Special thanks to
@peterseeberger
. What a fabulous institute!
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I am eternally grateful to Sam Gellman who, a while back, invited me to the Peptides GRC. I got introduced to peptide community. With no prior training in peptides by way of my academic upbringing, this is how we entered the field. Early-career opportunities to speak are huge.
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Having an awesome time at the
@GordonConf
GRS graduate student poster session. The level of science is tremendous. The whole event is run by grad students.
Someone just asked me if I am a grad student or postdoc. I love it.
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Pandas eat for about 12 hours a day. Given how much we consume these days, no wonder we are in a pand-emic.
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Retro-CH activation is when you inadvertently quench your Grignard reaction with water. It sounds so much more respectable.
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Ahead of his time... It seriously appears as if R. B. Woodward is checking his iPhone on this photo.
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Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light by
@Melchiorre_P
and colleagues
@ChemicalScience
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Gyms are closed... But here is the old and rusty set from my single days. Years ago my wife instructed me to throw away “this ugly crap”. Guess what? I didn’t.
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That a molecule does not survive column chromatography is no indication of its lack of synthetic utility. Sometimes there is a rush to make this connection. I always like to remind students that BuLi won’t do good on a column either (yet it is a reasonably successful reagent).
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Machine learning papers paint chemical intuition as bias. There is a definite negative undertone there.
But the point of learning organic chemistry is to acquire an intuitive feel for it. This is the ONLY reason for us to teach this subject.
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Here come Synthetic Half-Reactions (SHRs) in
@ChemicalScience
.
I discuss several new concepts to enable mechanism-driven reaction discovery by matching driving forces with uphill steps.
Search engines do not index intermediates (big gap).
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The contrasting reactivity of trans- vs. cis-azobenzenes with benzynes by Tom Hoye and co-workers
@UMNChemistry
@ChemicalScience
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An interrupted Corey–Chaykovsky reaction of designed azaarenium salts by Ramasastry and colleagues from IISER
@ChemicalScience
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Thank you
@NatureChemistry
for featuring our conformational dark space paper on the cover of their March issue.
Indebted to
@Ella_Maru
for her artistic expression of this chemistry. It has been fun to work with you, Ella!
Our March issue is live! On the cover is a paper from
@andrei_yudin
,
@DiegoBenDiaz
,
@gabepgomes
and co-workers (cover image from
@Ella_Maru
and in-house art editor Tulsi Voralia). Link to issue here:
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With Masa Inoue, Motomu Kanai, Hiro Suga, and Hiroki Oguri
@UTokyo_News
. What a great day of chemistry discussions... Here we are at after dinner drinks.
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I don’t like reading about toilet paper fights, but I respect creativity.
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Had great discussions with
@PhosphorusFive
at
@HumboldtUni
on his phosphorus chemistry. During the visit, Prof. Han Sun (really amazing NMR methodology!) told me about borolithochrome - a Jurassic era spiroborate, a rare boron-containing natural product.
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Was reminded by colleagues about review Kolb, M.G., and Barry wrote in 2001. It had a bunch of my unpublished (and unpublishable) work such as this gem they actually used in TOC (was a collaboration with Chi-Huey Wong on sugars). I did not have time to separate diastereomers...
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Is it possible to “lower a reaction barrier”? Not really, yet this wording persists.
One can replace a high barrier process with a lower one. Catalysts do that, this is how they increase reaction rates. But that is all we can say. No barrier can ever go down, it is what it is.
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Ambiphilicity of ring-expanded N-heterocyclic carbenes by Guy Bertrand and colleagues at
@UCSDChemBiochem
@ChemicalScience
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I mourn the untimely passing of my wonderful colleague, Prof. Deborah Zamble - a top-notch scientist, who made an important impact on metal homeostasis in biochemistry.
To battles of wits Deb would never come unarmed. She had a sharp sense of humour and made us smile.
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If students are keen on using what they know to make new antivirals now, just do it. Do not listen to people who say “too late”, “waste of time”.
Why Lipitor has that weird pyrrole in it? Bruce Roth (discoverer, Pfizer) was doing a lot of pyrrole chem in PhD. You never know.
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Went for a pint with my lab today. I proposed a RIP toast to a molecule that was on our target list for years (on and off). The structure appears to be too unstable for this world, although I am at no liberty to disclose it because my students still want to prove me wrong.
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Interrupted reactions are fascinating, yet there is no consensus on the meaning of this term. With
@vincent_trudel
, Alina, and Tien we take a close look at some of the "detours" and analyze what drives them.
@NatRevChem
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Occasional sarcasm about synthetic chemists still using archaic methods (round bottom flasks etc) for centuries without much change are hilarious.
We don’t lament on spoons, forks, knives, and chopsticks, do we? They work well, have done so for millennia, and will never go away.
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Students who are passionate about organic chemistry and want to pursue it as a career must draw a nicely balanced cycloheptane.
Yes. Must be a 7-membered ring drawn in one fell swoop. All bonds must be nearly equal in length. No weird angles. Can’t lift the chalk off the board.
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