Uploaded August 2022 | Updated September 2026, 3 weeks ago
This is a totally normal video about chemicals and is educational - nothing special to see here. 👼
Support the Channel on Patreon - patreon.com/thatchemist
Join the Community Discord! - discord.gg/thatchemist
Second Discord link if the first one is borked - discord.gg/QWNPETtPcZ
Clitoriacetal Reference - doi.org/10.1016/S0031-9422(98)00235-0
Charlie's video - youtube.com/watch?v=fByMGbFUZxE
Markiplier's video - youtube.com/watch?v=fBJ72GhkuFY
Molecules for this tierlist - Benzo[k]fluoranthene, Skatole, Fucitol, TATP, Phosgene, Phthalic Acid, Clitoracital, Methanal, Urospermal, Orotic acid, Spermine, Spermidine, Tetraethyllead, Pimpinellin, Limaspermidine, Hymenin, Methamphetamine, Viagra, Bastardane, Fagomine, Vaginidiol, Naled, & Lactate
This is a totally normal video about chemicals and is educational - nothing special to see here. 👼
Support the Channel on Patreon - patreon.com/thatchemist
Join the Community Discord! - discord.gg/thatchemist
Second Discord link if the first one is borked - discord.gg/QWNPETtPcZ
Clitoriacetal Reference - doi.org/10.1016/S0031-9422(98)00235-0
Charlie's video - youtube.com/watch?v=fByMGbFUZxE
Markiplier's video - youtube.com/watch?v=fBJ72GhkuFY
Molecules for this tierlist - Benzo[k]fluoranthene, Skatole, Fucitol, TATP, Phosgene, Phthalic Acid, Clitoracital, Methanal, Urospermal, Orotic acid, Spermine, Spermidine, Tetraethyllead, Pimpinellin, Limaspermidine, Hymenin, Methamphetamine, Viagra, Bastardane, Fagomine, Vaginidiol, Naled, & Lactate


![Five Important Papers in Organic Synthesis (July 2022)
In this video, I discuss five important papers in organic synthesis that were published in June 2022.
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Join the Community Discord! - https://discord.gg/thatchemist
Links to articles discussed in this episode:
Halogenation - https://www.doi.org/10.1021/jacs.2c06440
prior work - https://www.doi.org/10.1021/acs.joc.7b02920
Collybolide - https://www.doi.org/10.1021/acscentsci.2c00442
Trifluoromethylation - https://www.doi.org/10.1021/jacs.2c04807
Bipolamine I - https://www.doi.org/10.1021/jacs.2c06015
hydrogen autotransfer- https://www.doi.org/10.1021/acs.orglett.7b02336
Tricarbonyl-Ene - https://www.doi.org/10.1002/anie.202203311
Golec Oxidation - https://www.doi.org/10.1016/S0040-4039(00)60085-0
Benzoxazoles - https://www.doi.org/10.1021/acs.joc.2c00790
Cyclopropylamines - https://www.doi.org/10.1021/acs.orglett.2c01634
BCPs - https://www.doi.org/10.1021/jacs.2c05304
Inpyrfluxam - https://www.doi.org/10.1021/acs.oprd.2c00097
Indolylalcohols - https://www.doi.org/10.1021/jacs.2c02216
Sulfinimine Mannich - https://www.doi.org/10.1021/jacs.2c05368
Ar-CF2-[Si] - https://www.doi.org/10.1021/jacs.2c05044 Five Important Papers in Organic Synthesis (July 2022)](https://i.ytimg.com/vi/uxHZzCwEvmc/mqdefault.jpg)


![Dithioles - A Universal Scaffold for Organic Synthesis (Important Papers)
As there is no comprehensive reviews anywhere which showcase the versatility of these reagents, I decided to spill the beans on some of the best chemistry out there.
In this video, I share what is arguably the most versatile building block in organic synthesis - the dithiole. Its like a Corey dithiane but way easier to manipulate - need to make a carbonyl? Simply use Ag2O. Want a CH2? Use Raney nickel. Mild bases can be used once you start oxidizing the dithiole to the sulfoxide(s) and sulfone forms, meaning that they can readily be alkylated or coupled with various electrophiles. You can also make them react as carbenes (from the 2-chloro-sulfone, for example)!
Interested in synthetic consulting? Get in touch! More info at the end of the video. Interested sponsors are also encouraged to reach out.
Important Papers covers various chemical reactions, mechanisms, and research papers in the field of organic chemistry, providing examples and explanations for each research paper.
Support the Channel on Patreon - https://www.patreon.com/thatchemist
Important Papers Playlist - https://youtube.com/playlist?list=PL6OLqxmk7RtyRkdJhXK8NWpT1krGNq1p4
References:
Huge BDT review (1985; featuring some stuff which wasnt discussed here) - https://doi.org/10.1080/01961778508082475
Dioxygenase ref 1 - https://pubs.acs.org/doi/10.1021/ja00049a004
Dioxygenase ref 2 - https://doi.org/10.1016/j.tet.2003.10.107
dithiole oxidation to sulfoxide, sulfone, and carbene chem - https://doi.org/10.1016/S0040-4020(01)90393-X
Dithiole monosulfoxide chlorination - https://doi.org/10.1055/s-1985-31261
Lithiation of dithiole with trapping by aldehydes and ketones - https://doi.org/10.1016/j.tet.2003.10.107 (the dioxygenase paper)
Another aldehyde/ketone paper which I dont have the DOI of - Brown, Charles Allan; Chapa, O.; Yamaichi, A.[Heterocycles, 1982, vol. 18, p. 187 - 189]
Fluorination of the dithiole bis-sulfone with selectfluor - https://doi.org/10.1002/anie.200906866
N-parameters of bis-sulfone and fluoro bis-sulfone (they dinked up the figure and had to submit a correction btw) - https://doi.org/10.1002/anie.201605616
1,2- and 1,4- substitution of the fluoro bis sulfone - https://doi.org/10.1002/anie.200906866
Eeros BDT-BF4 - https://doi.org/10.1002/047084289X.rb027
Tributyltin hydride on the BDT ether and amines - https://pubs.acs.org/doi/10.1021/jo00003a052
Adding in the mono sulfoxide into nitroarenes - https://doi.org/10.1080/10426509308036881
imine scandium triflate cyclization - https://pubs.acs.org/doi/10.1021/ol020179d
chloro bis-methyl acetal dithiafulvalene synthesis from dithiol - https://doi.org/10.1002/jhet.5570310676
intramolecular domino cyclization of dithiafulvalene (aka EAS reaction) - https://doi.org/10.1021/jo00304a021
^paper also discusses the chemoselective transformations from slide 30
indole functionalization of DMBDT, difluoroether synthesis, radiofluorination, etc - https://doi.org/10.1002/chem.202202862
My PhD thesis New Fluorination Strategies and Reagents -
https://summit.sfu.ca/item/37816
Trityl BF4 synthesis - https:doi.org/10.1055/s-1972-21914 (the other ways using carboxylic acid anhydrides suffer from purification issues - it is easier to do it this way if you dont hate yourself)
Eeros Trityl BF4 Review - https://doi.org/10.1002/047084289X.rt362.pub2
TTF/DTF article 1 - https://link.springer.com/article/10.1007/s007060200074
TTF/DTF article 2 - https://doi.org/10.1002/chem.201802744
Dear materials scientists, please make 1 product with dithiafulvalenes or tetrathiafulvalenes by 2030, otherwise the organic chemists will think you are clowning
MW Dictionary - Fraud (Noun)
Synonyms of fraud
: deceit, trickery
specifically : intentional perversion of truth in order to induce another to part with something of value or to surrender a legal right
: an act of deceiving or misrepresenting : trick Dithioles - A Universal Scaffold for Organic Synthesis (Important Papers)](https://i.ytimg.com/vi/vLjEdrvji3c/mqdefault.jpg)




