In @science.org this week, Indrajeet Sharma’s group report a versatile reagent to slide nitrogen into 5-membered N-heterocycles
chemsky 🧪
www.science.org/doi/10.1126/...
chemsky 🧪
www.science.org/doi/10.1126/...
Sulfenylnitrene-mediated nitrogen-atom insertion for late-stage skeletal editing of N-heterocycles
Given the prevalence of nitrogen-containing heterocycles in commercial drugs, selectively incorporating a single nitrogen atom is a promising scaffold hopping approach to enhance chemical diversity in...
www.science.org
January 2, 2025 at 7:31 PM
In @science.org this week, Indrajeet Sharma’s group report a versatile reagent to slide nitrogen into 5-membered N-heterocycles
chemsky 🧪
www.science.org/doi/10.1126/...
chemsky 🧪
www.science.org/doi/10.1126/...
Unusual heterocycles and biosynthesis of natural products, published today in Communications Chemistry 🧵
December 19, 2024 at 2:46 PM
Unusual heterocycles and biosynthesis of natural products, published today in Communications Chemistry 🧵
A new way to make the often-elusive medium-sized-ring heterocycles:
The Rings Less Traveled
www.science.org
December 5, 2024 at 6:02 PM
A new way to make the often-elusive medium-sized-ring heterocycles:
Why? Why did you ask an LLM this?
See also: the Heterocycles debacle. The restrictive nature of your archiving strategy is very... questionable.
See also: the Heterocycles debacle. The restrictive nature of your archiving strategy is very... questionable.
We asked ChatGPT to tell us something inspirational about digital preservation today 1/4
July 9, 2026 at 5:05 PM
Why? Why did you ask an LLM this?
See also: the Heterocycles debacle. The restrictive nature of your archiving strategy is very... questionable.
See also: the Heterocycles debacle. The restrictive nature of your archiving strategy is very... questionable.
In @science.org this week, Ryan Steele and Motohiro Fujiu in @sarponggroup.bsky.social move an acyl group by transposing adjacent carbons rather than moving the oxygen 🔀
chemsky 🧪
www.science.org/doi/10.1126/...
chemsky 🧪
www.science.org/doi/10.1126/...
1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans
Saturated heterocycles are commonly adorned with groups that influence their biological properties. Synthetic methods that transpose existing substituents on saturated heterocycles to multiple periphe...
www.science.org
May 8, 2025 at 7:43 PM
In @science.org this week, Ryan Steele and Motohiro Fujiu in @sarponggroup.bsky.social move an acyl group by transposing adjacent carbons rather than moving the oxygen 🔀
chemsky 🧪
www.science.org/doi/10.1126/...
chemsky 🧪
www.science.org/doi/10.1126/...
Congratulations to Bi Youan Eric Tra on an excellent PhD Defense @mitchemistry.bsky.social and a thesis packed with X-ray crystal structures of novel boron heterocycles! Stay tuned for his next paper soon! @gilliardgroup.bsky.social
April 24, 2025 at 9:44 PM
Congratulations to Bi Youan Eric Tra on an excellent PhD Defense @mitchemistry.bsky.social and a thesis packed with X-ray crystal structures of novel boron heterocycles! Stay tuned for his next paper soon! @gilliardgroup.bsky.social
Boraindenes as versatile precursors to benzannulated boron heterocycles ( @LabBraunschweig ): pubs.rsc.org/en/content/a... ( @chemicalscience.rsc.org ).
December 9, 2025 at 8:52 PM
Boraindenes as versatile precursors to benzannulated boron heterocycles ( @LabBraunschweig ): pubs.rsc.org/en/content/a... ( @chemicalscience.rsc.org ).
Our collaborative paper on making uranium(IV) ketimides from U(III) reactions with N-heterocycles, lead by @conradgoodwin.bsky.social with the groups of @nfchilton.bsky.social, Steve Liddle, and others at MCR and ANU inc @john-seed.bsky.social, is now in @chemrxiv.org: chemrxiv.org/doi/full/10....
Reactions of a uranium(III) complex with N-heterocycles to form diuranium(IV) ketimides | ChemRxiv
The chemistry of the classical uranium(III) complex [U(N′′)3] (N′′ = {N(SiMe3)2}–) is well-developed, but there have been surprisingly few studies of its reactivity towards N-heterocycles. Here we report the separate reactions of [U(N′′)3] with pyrazine, ...
chemrxiv.org
April 6, 2026 at 8:25 AM
Our collaborative paper on making uranium(IV) ketimides from U(III) reactions with N-heterocycles, lead by @conradgoodwin.bsky.social with the groups of @nfchilton.bsky.social, Steve Liddle, and others at MCR and ANU inc @john-seed.bsky.social, is now in @chemrxiv.org: chemrxiv.org/doi/full/10....
Redox and Charge State Dependent Trends in Boron Heterocycles: A Neutral Ligand Coordination Chemistry Approach to Boracyclic Cations, Anions, and Radicals | Accounts of Chemical Research #ouryearinreview @gilliardgroup.bsky.social #maingroup #chemsky pubs.acs.org/doi/full/10....
Redox- and Charge-State Dependent Trends in 5, 6, and 7-Membered Boron Heterocycles: A Neutral Ligand Coordination Chemistry Approach to Boracyclic Cations, Anions, and Radicals
ConspectusBoron heterocycles represent an important subset of heteroatom-incorporated rings, attracting attention from organic, inorganic, and materials chemists. The empty pz orbital at the boron cen...
pubs.acs.org
December 18, 2024 at 1:40 PM
Redox and Charge State Dependent Trends in Boron Heterocycles: A Neutral Ligand Coordination Chemistry Approach to Boracyclic Cations, Anions, and Radicals | Accounts of Chemical Research #ouryearinreview @gilliardgroup.bsky.social #maingroup #chemsky pubs.acs.org/doi/full/10....
Medchem heterocycles:
Dislike: oxetane (closely followed by oxazole)
Overrated: BCP (yes I know it’s not a heterocycle)
Underrated: THF
Like: Pyrazole
Trust: Piperidine
#Chemsky
(Disclaimer: post is copied from the other place but a fun way to start…something)
Dislike: oxetane (closely followed by oxazole)
Overrated: BCP (yes I know it’s not a heterocycle)
Underrated: THF
Like: Pyrazole
Trust: Piperidine
#Chemsky
(Disclaimer: post is copied from the other place but a fun way to start…something)
December 20, 2024 at 4:48 AM
Medchem heterocycles:
Dislike: oxetane (closely followed by oxazole)
Overrated: BCP (yes I know it’s not a heterocycle)
Underrated: THF
Like: Pyrazole
Trust: Piperidine
#Chemsky
(Disclaimer: post is copied from the other place but a fun way to start…something)
Dislike: oxetane (closely followed by oxazole)
Overrated: BCP (yes I know it’s not a heterocycle)
Underrated: THF
Like: Pyrazole
Trust: Piperidine
#Chemsky
(Disclaimer: post is copied from the other place but a fun way to start…something)
One of the most important emails I have received for 2025. THANK YOU to the reviewers and panelists of our NSF proposal for believing in my group's scientific endeavors on PN-heterocycles (azaphosphinines) one more time. This will provide research funds for my group until fall 2028. #chemsky #pisky
May 23, 2025 at 10:20 PM
Congratulations to Sojung, our collaborator from the Sigman group Jordan, our collaborators from Merck and former group members Justin and Yasuki on the publication of our work on understanding the enantioselectivity of our photomediated ring contraction in JACS!
doi.org/10.1021/jacs...
doi.org/10.1021/jacs...
Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles
We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding a single heteroatom from a r...
doi.org
January 3, 2025 at 3:21 AM
Congratulations to Sojung, our collaborator from the Sigman group Jordan, our collaborators from Merck and former group members Justin and Yasuki on the publication of our work on understanding the enantioselectivity of our photomediated ring contraction in JACS!
doi.org/10.1021/jacs...
doi.org/10.1021/jacs...
Precursors to Life
Precursors to life? 🧬 Curiosity detected nitrogen heterocycles on Mars for the first time—structures considered predecessors to RNA and DNA. This discovery confirms that ancient Mars had the right chemical toolkit to potentially support life. #Astrobiology #Mars #Science
2/4
Precursors to life? 🧬 Curiosity detected nitrogen heterocycles on Mars for the first time—structures considered predecessors to RNA and DNA. This discovery confirms that ancient Mars had the right chemical toolkit to potentially support life. #Astrobiology #Mars #Science
2/4
April 21, 2026 at 8:26 PM
Precursors to Life
Precursors to life? 🧬 Curiosity detected nitrogen heterocycles on Mars for the first time—structures considered predecessors to RNA and DNA. This discovery confirms that ancient Mars had the right chemical toolkit to potentially support life. #Astrobiology #Mars #Science
2/4
Precursors to life? 🧬 Curiosity detected nitrogen heterocycles on Mars for the first time—structures considered predecessors to RNA and DNA. This discovery confirms that ancient Mars had the right chemical toolkit to potentially support life. #Astrobiology #Mars #Science
2/4
Rreactivity of Pnictaalumenes towards 1,3-Dipole Molecules fresh out in @angewandtechemie.bsky.social Tim, Edgar and Leonie uncover unique insertion chemsitry giving a plethora of Al,P,N-heterocycles! Again a fruitful collaboration with the Braunschweig Group!
doi.org/10.1002/anie...
doi.org/10.1002/anie...
April 10, 2025 at 3:21 PM
Rreactivity of Pnictaalumenes towards 1,3-Dipole Molecules fresh out in @angewandtechemie.bsky.social Tim, Edgar and Leonie uncover unique insertion chemsitry giving a plethora of Al,P,N-heterocycles! Again a fruitful collaboration with the Braunschweig Group!
doi.org/10.1002/anie...
doi.org/10.1002/anie...
Our (Gilliard/Cummins labs) manuscript on the generation of transient, sterically unhindered multiply bonded boron species is now published in @chemicalscience.rsc.org! Chonghe reports an array of new boron heterocycles! #maingroup pubs.rsc.org/en/content/a...
May 21, 2025 at 4:57 PM
Our (Gilliard/Cummins labs) manuscript on the generation of transient, sterically unhindered multiply bonded boron species is now published in @chemicalscience.rsc.org! Chonghe reports an array of new boron heterocycles! #maingroup pubs.rsc.org/en/content/a...
Our latest paper in collaboration with the Liddle, @nfchilton.bsky.social and @conradgoodwin.bsky.social groups investigating uranium ketimides is now published in Inorganic Chemistry, with @john-seed.bsky.social and other Manchester and ANU Chemistry peeps: pubs.acs.org/doi/10.1021/...
Reactions of a Uranium(III) Complex with N-Heterocycles to Form Diuranium(IV) Ketimides
The chemistry of the classical uranium(III) complex [U(N″)3] (N″ = {N(SiMe3)2}−) is well-developed; however, there have been surprisingly few studies of its reactivity toward N-heterocycles. Here, we ...
pubs.acs.org
June 8, 2026 at 10:56 AM
Our latest paper in collaboration with the Liddle, @nfchilton.bsky.social and @conradgoodwin.bsky.social groups investigating uranium ketimides is now published in Inorganic Chemistry, with @john-seed.bsky.social and other Manchester and ANU Chemistry peeps: pubs.acs.org/doi/10.1021/...
Chemists at the University of California, Davis, led by Jared T. Shaw and Dean J. Tantillo report a new way to cyclize sulfonimidamides to make rare five-membered heterocycles that are both aromatic and chiral.
#chemsky 🧪
#chemsky 🧪
Reaction rounds up atoms into unusual cyclic compounds
Chiral aromatic heterocycles could be novel motifs in drug candidates
cen.acs.org
July 28, 2026 at 1:49 PM
Chemists at the University of California, Davis, led by Jared T. Shaw and Dean J. Tantillo report a new way to cyclize sulfonimidamides to make rare five-membered heterocycles that are both aromatic and chiral.
#chemsky 🧪
#chemsky 🧪
Just in time for the new year - we show that you can make either isomer of N-aryl pyrazole selectively from a single TDSO. We really believe in the power of these wacky heterocycles.
chemrxiv.org/engage/chemr...
Excellent work by superstar Alex Fanourakis, in collab with Osvaldo Gutierrez and J&J
chemrxiv.org/engage/chemr...
Excellent work by superstar Alex Fanourakis, in collab with Osvaldo Gutierrez and J&J
December 30, 2025 at 2:26 PM
Just in time for the new year - we show that you can make either isomer of N-aryl pyrazole selectively from a single TDSO. We really believe in the power of these wacky heterocycles.
chemrxiv.org/engage/chemr...
Excellent work by superstar Alex Fanourakis, in collab with Osvaldo Gutierrez and J&J
chemrxiv.org/engage/chemr...
Excellent work by superstar Alex Fanourakis, in collab with Osvaldo Gutierrez and J&J
Congratulations to Ryan and Moto on the publication of their 1,2-acyl transposition in 2,3-dihdyrobenzofurans in @science.org!
www.science.org/doi/10.1126/...
www.science.org/doi/10.1126/...
1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans
Saturated heterocycles are commonly adorned with groups that influence their biological properties. Synthetic methods that transpose existing substituents on saturated heterocycles to multiple peripheral positions are therefore highly valuable. In this ...
www.science.org
May 8, 2025 at 11:17 PM
Congratulations to Ryan and Moto on the publication of their 1,2-acyl transposition in 2,3-dihdyrobenzofurans in @science.org!
www.science.org/doi/10.1126/...
www.science.org/doi/10.1126/...
Access to Nitrogen–nitrogen Bond-Containing Heterocycles Through Substrate Promiscuity of Piperazate Synthases | ACS Catalysis pubs.acs.org/doi/10.1021/...
Access to Nitrogen–nitrogen Bond-Containing Heterocycles Through Substrate Promiscuity of Piperazate Synthases
The nitrogen–nitrogen (N–N) bond motif comprises an important class of compounds for drug discovery. Synthetic methods are primarily based on the modification of N–N or N═N precursors, whereas selecti...
pubs.acs.org
May 12, 2025 at 5:55 PM
Access to Nitrogen–nitrogen Bond-Containing Heterocycles Through Substrate Promiscuity of Piperazate Synthases | ACS Catalysis pubs.acs.org/doi/10.1021/...
We were granted and happy to welcome Dr David Leboeuf from LIMA Strasbourg and Pr Isabelle Gillaizeau from Orleans for great conferences ! 👍😊🤩 HFIP magic solvent and metal-catalyzed heterocycles synthesis on the program !! 🥰🥰🥰 @icn-cnrs.bsky.social @univcotedazur.bsky.social
March 12, 2025 at 10:20 PM
We were granted and happy to welcome Dr David Leboeuf from LIMA Strasbourg and Pr Isabelle Gillaizeau from Orleans for great conferences ! 👍😊🤩 HFIP magic solvent and metal-catalyzed heterocycles synthesis on the program !! 🥰🥰🥰 @icn-cnrs.bsky.social @univcotedazur.bsky.social
Umm p cool “We detected amino acids (including 14 of the 20 used in terrestrial biology), amines, formaldehyde, carboxylic acids, polycyclic aromatic hydrocarbons and N-heterocycles (including all five nucleobases found in DNA and RNA), along with ~10,000 N-bearing chemical species.”
January 31, 2025 at 11:33 AM
Umm p cool “We detected amino acids (including 14 of the 20 used in terrestrial biology), amines, formaldehyde, carboxylic acids, polycyclic aromatic hydrocarbons and N-heterocycles (including all five nucleobases found in DNA and RNA), along with ~10,000 N-bearing chemical species.”