Organic & Biomolecular Chemistry Blog

We are delighted to welcome Professor Judy I-Chia Wu to the Organic & Biomolecular Chemistry Editorial Board!

Judy earned a BS (2004) in Chemistry from Tunghai University, Taiwan, and a PhD (2011) working with Professor Paul Schleyer, at the University of Georgia. In 2015, she began her independent career at the University of Houston, Department of Chemistry. She has received an IUPAC Young Chemist Award, an NSF CAREER Award, and an NIH MIRA award. She was selected as a Sloan Research Fellow in 2020.

Her current research interests span topics in ground and excited-state aromaticity and antiaromaticity, photochemistry, supramolecular chemistry, and enzyme catalysis.

She enjoys long walks with her dog, and writing from a cozy corner.

See some of Judy’s recent research highlights in this Chemistry World article:

Or find out more by browsing a few of her recent publications:

On the reciprocal relationship between σ-hole bonding and (anti)aromaticity gain in ketocyclopolyenes
Hari Ram Paudel, Lucas José Karas and Judy I-Chia Wu
Org. Biomol. Chem., 2020,18, 5125-5129

Antiaromaticity gain increases the potential for n-type charge transport in hydrogen-bonded π-conjugated cores
Zhili Wen and Judy I-Chia Wu
Chem. Commun., 2020,56, 2008-2011

How does excited-state antiaromaticity affect the acidity strengths of photoacids?
Zhili Wen, Lucas José Karas, Chia-Hua Wu and Judy I-Chia Wu
Chem. Commun., 2020,56, 8380-8383

Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing
Yu Zhang, Chia-Hua Wu and Judy I-Chia Wu
Org. Biomol. Chem., 2019,17, 1881-1885

Superalkali ligands as a building block for aromatic trinuclear Cu(I)–NHC complexes
Rakesh Parida, Subhra Das, Lucas José Karas, Judy I-Chia Wu, Gourisankar Roymahapatra and Santanab Giri
Inorg. Chem. Front., 2019,6, 3336-3344

Mixed-carbene cyclometalated iridium complexes with saturated blue luminescence
Hanah Na, Louise M. Cañada, Zhili Wen, Judy I-Chia Wu and Thomas S. Teets
Chem. Sci., 2019,10, 6254-6260

Azo-triazolide bis-cyclometalated Ir(III) complexes via cyclization of 3-cyanodiarylformazanate ligands
Ge Mu, Zhili Wen, Judy I-Chia Wu and Thomas S. Teets
Dalton Trans., 2020,49, 3775-3785

Introducing the researchers:

Bo Xu was born in Hubei, China, after receiving his Ph.D. degree from the University of Louisville in 2008 (research advisor Prof. Gerald B. Hammond), he worked as a research assistant professor at the University of Louisville until 2014. He is currently a professor in the College of Chemistry, Chemical Engineering and Biotechnology, Donghua University Shanghai, China. His research interests include the development of novel and environmentally friendly synthetic methodologies, especially the synthesis of novel fluorinated building blocks for drugs and advanced materials and studies of organic reaction mechanisms.

Gerald B. Hammond was born in Lima, Perú, received his B.Sc from the Pontifical Catholic University of Perú, his M.Sc from the University of British Columbia (Canada), and his Ph.D. from the University of Birmingham in England. Following an academic career at the University of Massachusetts Dartmouth, Professor Hammond moved to the University of Louisville in 2004, where he is currently Endowed Chair in Organic Chemistry. His research interests include the search for new synthetic methodologies in organofluorine chemistry and other halogens, new approaches to catalysis and green chemistry, and the study of biologically active natural products from Peruvian medicinal plants.

Zhichao Lu was born in Hubei, China. he joined the doctoral program at the University of Louisville in 2013 under the supervision of Professor Gerald B. Hammond and Professor Bo Xu. He obtained a Ph.D. degree in 2018 and continued postdoctoral research program in the same lab.  His current research interests involve the development of novel gold catalysts and new fluorinating reagents.

What inspired your research in this area?

We have a long-term interest in acid and hydrogen bonding catalysis; as such, we wanted to explore the role of acid and hydrogen bonding donor in enamine catalysis.

What do you personally feel is the most interesting outcome of your study?

Acid catalyst is often used in enamine formation. We found that, in many cases, strong acids are not necessary for enamine formation and the use of acids may even destabilize enamines.

What directions are you planning to take with your research in future?

Enamine formation is just the first step of the catalytic cycle of enamine catalysis; we want to explore the role of acids and hydrogen bonding donors in the full catalytical cycle of enamine catalysis.

Read the full article: Revisiting the role of acids and hydrogen bond acceptors in enamine formation

See the other articles showcased in this month’s Editor’s Collection

See all the full articles on our publishing platform

New OBC Associate Editor Xiaohua Liu

Organic & Biomolecular Chemistry is delighted to welcome Professor Xiaohua Liu as an Associate Editor from 1^st of August 2020.

Xiaohua Liu obtained her BSc degree from Hubei Normal University (2000), and obtained her MS (2003) and PhD (2006) from Sichuan University. She joined the faculty of Prof. Feng’s group in 2006, and was appointed as an associate professor. In 2010, she was promoted as a full professor. Her current research interests include asymmetric catalysis and chiral drug synthesis.

To find out more about Xiaohua Liu and her achievements, you can visit the webpage or browse some of her publications below.

Xiaohua’s publications with Organic & Biomolecular Chemistry:

Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde
Org. Biomol. Chem., 2016, 14, 5914-5917

Chiral biphenylamide derivative: an efficient organocatalyst for the enantioselective synthesis of α-hydroxy phosphonates
Org. Biomol. Chem., 2009, 7, 4355-4357

Reversal of enantioselectivity in chiral metal complex-catalyzed asymmetric reactions
Org. Biomol. Chem., 2019, 17, 6538-6550

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy
Org. Biomol. Chem., 2016, 14, 5258-5262

Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diaminecatalysts based on bispidine
Org. Biomol. Chem., 2009, 7, 4120-4127

Highly enantioselective synthesis of γ-substituted butenolidesvia the vinylogous Mukaiyama–Michael reaction catalyzed by a chiral scandium(iii)–N,N′-dioxide complex
Org. Biomol. Chem., 2011, 9, 5748-5754

Organic & Biomolecular Chemistry (OBC) is proud to be sponsoring the 16th Annual Tri-Institutional Chemical Biology Symposium, which will take place virtually on the 1st of September, 2020 09:00-18:30 EDT.

This event showcases research at the forefront of chemical biology, and is sponsored and organized by the Tri-Institutional PhD Program in Chemical Biology (TPCB), a joint graduate program of Memorial Sloan Kettering Cancer Center, The Rockefeller University, and Weill Cornell Medicine in New York City.

Register for this free event here by the 28th of August 2020.

Undergraduate students interested in chemical biology are especially encouraged to attend.

Poster submissions are welcomed from all attendees, including early college high school students, undergraduates, postbaccalaureate students, research assistants and technicians, graduate students, postdoctoral fellows, research staff, and faculty. Posters will be presented live by video in parallel meeting rooms, and judged by TPCB faculty members and keynote speakers for a selection of poster awards sponsored by TPCB and their promotional partners, including RSC Chemical Biology, Chemical Science and Organic & Biomolecular Chemistry.

For more information, please visit the Tri-Institutional Chemical Biology Symposium event page.

TPCB has been strongly committed to diversity and inclusion since its inception. It welcomes scientists from underrepresented minority groups and disadvantaged backgrounds, and those with disabilities.  It does not tolerate racism, discrimination, or harassment of any kind. All attendees are expected to maintain the highest standards of professional conduct throughout the symposium.

We would like to highlight the Outstanding Reviewers for Organic & Biomolecular Chemistry in 2019, as selected by the editorial team, for their significant contribution to the journal. The reviewers have been chosen based on the number, timeliness and quality of the reports completed over the last 12 months.

We would like to say a big thank you to those individuals listed here as well as to all of the reviewers that have supported the journal. Each Outstanding Reviewer will receive a certificate to give recognition for their significant contribution.

Prof. Dr. Jeroen Dickschat, University of Bonn, ORCHID: 0000-0002-0102-0631

Dr Jianlin Han, Nanjing Forestry University, ORCHID: 0000-0002-3817-0764

Professor Erhong Hao, Anhui Normal University, ORCHID: 0000-0001-7234-4994

Dr Mohammed Hasan, Tallinn University of Technology, ORCHID: 0000-0001-5683-6673

Prof. Dr. Hans-Joachim Knölker, Technische Universität Dresden, ORCHID: 0000-0002-9631-5239

Dr Rafal Loska, Polish Academy of Sciences, ORCHID: 0000-0002-0823-4675

Professor Vaibhav P. Mehta, Marwadi University, ORCHID: 0000-0003-4426-3374

Dr Tej Narayan Poudel, University of Minnesota, ORCHID: 0000-0002-0390-107X

Professor Akhilesh K. Verma, University of Delhi, ORCHID: 0000-0001-7626-5003

Dr Chunxiang Wang, Takeda Pharmaceutical Co Ltd, ORCHID: 0000-0002-8669-1767

We would also like to thank the Organic & Biomolecular Chemistry board and the organic chemistry community for their continued support of the journal, as authors, reviewers and readers.

If you would like to become a reviewer for our journal, just email us with details of your research interests and an up-to-date CV or résumé.  You can find more details in our author and reviewer resource centre

Organic & Biomolecular Chemistry and our sister journals, Chemical Science and RSC Advances, are proud to sponsor the upcoming Chemical Biology and Physiology Conference, 12-15 December 2019 at Oregon Health & Science University.

Compounds containing carbon-boron bonds are of high significance because they can be used as the precursors for various reactions such as 1,2-metallate rearrangements, deborylative nucleophilic addition reactions and the formation of carbon-oxygen and carbon-nitrogen bonds through hydrolysis and aminolysis respectively. Sulfones are useful for increasing the functionality of a molecule by alkylation and arylation (scheme 1), however till date there have been very few reports regarding the transformation of carbon-sulfonyl bonds to carbon-boron bonds. The transformation of sulfonyl groups to boryl groups under metal free organocatalysis is still a challenging task.

Scheme 1: Sequential functionalization of benzylic sulfones

In their recent OBC publication, Prof Cathleen M. Crudden et.al. of Queen’s University, Ontario developed a beautiful protocol for the transition metal-free desulfonative borylation of benzyl sulfones using simple pyridine derivatives as catalysts (scheme 2). They reported the borylation of cyclic sulfones to afford functionalized sulfones and sulfonamides through a sulfinate intermediate which could be trapped with electrophiles. As they chose benzhydryl phenyl sulfone (1a) as a model substrate for their optimization, they reported the formation of the desired dibenzylic boronic (2a) ester along with diphenylmethane (3a) as a by-product. By using trifluorotoluene as a solvent instead of ethereal solvents, they optimized their conditions, resulting in an enhanced formation of 2a and supressed formation of 3a.

Scheme 2: Pyridine-promoted desulfonative borylation of benzyl sulfones

The reaction was well tolerated by a range of benzhydryl sulfones bearing both electron-neutral and electron-rich aryl groups with good yields. Even sterically hindered ortho-substituted aryl groups also afforded the desired products with lower yields. Unfortunately, benzhydryl sulfones bearing electron-withdrawing substituents such as trifluoromethyl, esters, cyano, allyl and iodide groups were not tolerated the transformation. Crudden et. al. executed control experiments in order to understand the reaction mechanism, finding that the sulfone bearing terminal olefin did not afford any product and also that TEMPO ((2,2,6,6-Tetramethylpiperidin-1-yl)oxyl) completely inhibited borylation. Based on these observations, they proposed a single electron transfer mechanism for borylation based on the work from Tuttle and Zhang and Jiao.

In conclusion, Crudden et al. succeeded in developing a desulfonylative borylation of alkyl sulfon es through 4-arylpyridine catalysis which yields synthetically useful benzylic boron compounds.

Read their full article now.

About the Blog Writer: A. Vamshi Krishna is currently pursuing a Ph.D. in organic chemistry with Prof. D. B. Ramachary at University of Hyderabad. His research mainly focuses on asymmetric supramolecular-organocatalysis, where he synthesises highly functionalized biologically active novel scaffolds with excellent selectivities and yields. His passion for scientific writing made him become a blog writer.

Nowadays, chemists are increasingly interested in revealing simpler methodologies for the synthesis of various drugs with high selectivity and purity. Transition metal catalysis has opened a wide window for the synthesis of different natural products and drugs with greater ease.

Z-Tamoxifen is one such drug, which is used in the treatment of breast cancer. Although there are many well-established synthetic procedures for the synthesis of Z-tamoxifen by various research groups such as T. Stiidemann et.al. and P. L. Coe et.al. etc., there are disadvantages to current methods, such as the use of multiple synthetic steps and generation of stoichiometric amounts of waste. Thus, there is a need to overcome these drawbacks.

In their recent OBC publication, Prof. Ben L. Feringa et.al. of Stratingh Institute for Chemistry, University of Groningen, Nijenborgh develop a fantastic two step protocol for the synthesis of Z-tamoxifen from commercially available starting materials. Usually, the transmetallation of anions formed by carbolithiation of (diphenyl)acetylenes with magnesium, boron, zinc or aluminium results in an active cross coupling partner, but with low atom efficiency. Here, Feringa et.al., for the first time proposed the direct cross coupling of the formed organolithium reagent with aryl halides in the presence of an active palladium nanoparticle based catalyst, cutting down the number of synthetic steps required to two, with excellent selectivities and yields. They report the thorough screening of reaction conditions such as solvent, temperature, catalyst loading etc. and explain the effect of various reaction parameters. The 0.67 atom economy and 22% RME achieved in the study is twice as good as the previously reported best protocol, and the scientists found that THF gave the desired product without encouraging any side reactions. Another advantage of this reaction is that the formed side product (lithium halide) can be easily removed.

Hence, Prof. Ben L. Feringa laid a new efficient pathway for the synthesis of biologically important Z-tamoxifen through his works.

Read their full article now.

About the Blog Writer: A. Vamshi Krishna is currently pursuing a PhD  in Organic chemistry with Prof. D. B. Ramachary at University of Hyderabad. His research mainly focuses on asymmetric supramolecular catalysis and organocatalysis, where he synthesises highly functionalized biologically active novel scaffolds with excellent selectivities and yields. He is passionate about scientific writing.

Organic & Biomolecular Chemistry are proud to sponsor the 2019 Bristol Synthesis Meeting, to be held in the Victoria Rooms, University of Bristol, 9th April 2019.

The meeting boasts a fantastic line up of speakers including OBC Advisory Board members Helma Wennemers (ETH Zurich) and Ilan Marek (Technion, Israel Institute of Technology).

Registration is now open, so for the full list of speakers and to register, see the Bristol Synthesis Meeting webpage.

Photoswitchable small molecules have become important tools for analyzing biological systems. The discovery of light-tuneable molecules has enabled the study of intricate physiological responses within cells through precise spatial and temporal control to modulate their function. Although powerful tools, de novo design is often challenging as it requires detailed information about the structure of both the ligand and the receptor.

In a recent OBC publication, the group of Professor Ratmir Derda of the University of Alberta discusses a strategy to develop libraries of light-responsive (LR) ligands, which can be produced by grafting known LR structures, such as azobenzene, onto molecules with established biological activity. In this way, the challenges of identifying novel LR ligands can be addressed by selecting from a library of tagged LR-compounds that are already known to possess desired biological function.

Their study outlines a proof-of-concept for such a library using the synthesis of LR-bicyclic peptides, which contain a hydroxyl amine and di-chlorobenzene containing azobenzene (HADCAz) linker.

HADCAz behaves as a 3-point linchpin and can be used in the bicyclization of peptides through its orthogonally reactive ‘thiol-reactive’ and ‘aldehyde-reactive’ attachment points. The authors successfully demonstrated the synthesis of a small library of bicyclic peptides from linear, unprotected peptides (~20 amino acids in length) in a one-pot, two step reaction involving double intramolecular nucleophilic addition and oxime formation to form the two loops. The peptide-bound HADCAz linkers were shown to reversibly switch to their cis-conformers after irradiation with 365 nm light and molecular dynamic (MD) simulation was used to assess conformational changes, the properties of which were seemingly dependent on the peptide’s length.

While optimizations are still required for broad application, this work provides a versatile platform from which numerous avenues within the realms of optochemical genetics and photo-pharmacology can be explored.

To find out more see:

Light-responsive bicyclic peptides
Mohammad R. Jafari, Hongtao Yu, Jessica M. Wickware, Yu-Shan Lin and  Ratmir Derda
DOI:10.1039/C7OB03178E

Victoria Corless is currently completing her Ph.D. in organic chemistry with Prof. Andrei Yudin at the University of Toronto. Her research is centred on the synthesis of kinetically amphoteric building blocks which offer a versatile platform for the development of chemoselective transformations with particular emphasis on creating novel biologically active molecules.