Organic Chemistry Frontiers Blog

We are delighted to highlight the following highly cited research articles published in Organic Chemistry Frontiers since 2023. We hope you enjoy reading them.

	Photoelectrochemical upcycling of PVC plastic waste for the synthesis of chlorinated quinolinone derivatives Kai Zheng, Jingwen He, Lixi Zhang, Zhaoyang Wang, Pengfei Zhang, Jianyu Cao and Chao Shen Org. Chem. Front., 2025,12, 3191-3197 https://doi.org/10.1039/D5QO00189G
	Energy-transfer photocatalysis for Minisci C–H (amino)alkylation of heteroarenes using oxime esters as dual-role reagents Jun Xu, Yuru Zhang, Ruiyuan Xu, Yuxin Wang, Jiabin Shen and Wanmei Li Org. Chem. Front., 2024,11, 5122-5129 https://doi.org/10.1039/D4QO00836G
	Arylgermylation of alkenes by a cooperative photoactivation and hydrogen atom transfer strategy Jia Cao, Yan Liu, Zhixiang Wang and Le Liu Org. Chem. Front., 2024,11, 7098-7106 https://doi.org/10.1039/D4QO01497A
	(±)-Hypandrone A, a pair of polycyclic polyprenylated acylphloroglucinol enantiomers with a caged 7/6/5/6/6 pentacyclic skeleton from Hypericum androsaemum Jiangchun Wei, Pingping Fan, Yahui Huang, Hanxiao Zeng, Rui Jiang, Zhengzhi Wu, Yonghui Zhang and Zhengxi Hu Org. Chem. Front., 2024,11, 3459-3464 https://doi.org/10.1039/D4QO00444B
	Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer Jun Xu, Yu Hong, Ruiyuan Xu, Yuxin Wang, Yirui Guo, Jiabin Shen, Yuxuan Zhao and Wanmei Li Org. Chem. Front., 2024,11, 6166-6176 https://doi.org/10.1039/D4QO01351D
	Access to spiro-bicyclo[2.1.1]hexanes via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes Jia-Yi Su, Jian Zhang, Zhi-Yun Xin, Hao Li, Hanliang Zheng and Wei-Ping Deng Org. Chem. Front., 2024,11, 4539-4545 https://doi.org/10.1039/D4QO00511B
	Iron-catalyzed fragmentation-alkynylation, -alkenylation and -alkylation cascade enabled by photoinduced ligand-to-metal charge transfer Yining Zhu, Han Gao, Jia-Lin Tu, Chao Yang, Lin Guo,Yating Zhao and Wujiong Xia Org. Chem. Front., 2024,11, 1729-1735 https://doi.org/10.1039/D3QO01822A
	Photoinduced C–H heteroarylation of enamines via quadruple cleavage of CF2Br2 Wanqing Zuo, Lingling Zuo, Xiao Geng, Zhifang Li and Lei Wang Org. Chem. Front., 2023,10, 6112-6116 https://doi.org/10.1039/D3QO01474F
	An iron-catalyzed C–S bond-forming reaction of carboxylic acids and hydrocarbons via photo-induced ligand to metal charge transfer Ao-Men Hu, Jia-Lin Tu, Mengqi Luo, Chao Yang, Lin Guo and Wujiong Xia Org. Chem. Front., 2023,10, 4764-4773 https://doi.org/10.1039/D3QO01081C
	Nickel-catalyzed cross-electrophile coupling of aryl thiols with aryl bromides via C–S bond activation Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou and Zhi-Liang Shen Org. Chem. Front., 2023,10, 5171-5179 https://doi.org/10.1039/D3QO01236K

We are delighted to highlight the following highly cited review articles published in Organic Chemistry Frontiers since 2023. We hope you enjoy reading them.

	Remodelling molecular frameworks via atom-level surgery: recent advances in skeletal editing of (hetero)cycles Rubal Sharma, Mitsuhiro Arisawa, Shinobu Takizawa and Mohamed S. H. Salem Org. Chem. Front., 2025,12, 1633-1670 https://doi.org/10.1039/D4QO02157F
	Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds Zi-Qi Zhu, Tian-Zhen Li, Si-Jia Liu and Feng Shi Org. Chem. Front., 2024,11, 5573-5604 https://doi.org/10.1039/D4QO00515E
	Advances in photoinduced radical–polar crossover cyclization (RPCC) of bifunctional alkenes Meng Liu, Xinke Ouyang, Chenglong Xuan and Chao Shu Org. Chem. Front., 2024,11, 895-915 https://doi.org/10.1039/D3QO01929B
	Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects Jia-Lin Tu, Yining Zhu, Pengcheng Li and Binbin Huang Org. Chem. Front., 2024,11, 5278-5305 https://doi.org/10.1039/D4QO01179A
	Recent advances in carbon atom addition for ring-expanding single-atom skeletal editing Ting Yuan and Lei Shi Org. Chem. Front., 2024,11, 7318-7332 https://doi.org/10.1039/D4QO01806K
	Modern photo- and electrochemical approaches to aryl radical generation Krzysztof Grudzień, Andrei Zlobin, Jan Zadworny, Katarzyna Rybicka-Jasińska and Bartłomiej Sadowski Org. Chem. Front., 2024,11, 5232-5277 https://doi.org/10.1039/D4QO00999A
	Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation Zefeng Jin, Fangfang Zhang, Xiao Xiao, Nengzhong Wang, Xin Lv and Liejin Zhou Org. Chem. Front., 2024,11, 2112-2133 https://doi.org/10.1039/D3QO02098C
	Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation Jianchao Liu, Jie-Ping Wan and Yunyun Liu Org. Chem. Front., 2024,11, 597-630 https://doi.org/10.1039/D3QO01844J
	Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds Qinhui Wan, Zhongyi Zhang, Zhong-Wei Hou and Lei Wang Org. Chem. Front., 2023,10, 2830-2848 https://doi.org/10.1039/D3QO00408B
	Recent developments on 1,2-difunctionalization and hydrofunctionalization of unactivated alkenes and alkynes involving C–S bond formation Bo Dong, Jian Shen and Lan-Gui Xie Org. Chem. Front., 2023,10, 1322-1345 https://doi.org/10.1039/D2QO01699K
	Feng chiral N,N′-dioxide ligands: uniqueness and impacts Dian-Feng Chen and Liu-Zhu Gong Org. Chem. Front., 2023,10, 3676-3683 https://doi.org/10.1039/D3QO00566F

To celebrate the Year of the Snake, we are delighted to highlight some of the most popular articles published in Organic Chemistry Frontiers by corresponding authors based in countries celebrating the Chinese New Year.

We hope you enjoy reading these articles and wish you a happy and prosperous year of the Snake.

	Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds Zi-Qi Zhu, Tian-Zhen Li, Si-Jia Liu and Feng Shi Org. Chem. Front., 2024,11, 5573-5604 https://doi.org/10.1039/D4QO00515E
	Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects Jia-Lin Tu, Yining Zhu, Pengcheng Li and Binbin HuangOrg. Chem. Front., 2024,11, 5278-5305 https://doi.org/10.1039/D4QO01179A
	Advances in photoinduced radical–polar crossover cyclization (RPCC) of bifunctional alkenes Meng Liu, Xinke Ouyang, Chenglong Xuan and Chao Shu Org. Chem. Front., 2024,11, 895-915 https://doi.org/10.1039/D3QO01929B
	Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation Zefeng Jin, Fangfang Zhang, Xiao Xiao, Nengzhong Wang, Xin Lv and Liejin Zhou Org. Chem. Front., 2024,11, 2112-2133 https://doi.org/10.1039/D3QO02098C
	Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer Jun Xu, Yu Hong, Ruiyuan Xu, Yuxin Wang, Yirui Guo, Jiabin Shen, Yuxuan Zhao and Wanmei Li Org. Chem. Front., 2024,11, 6166-6176 https://doi.org/10.1039/D4QO01351D
	Photoinduced difunctionalizations of unactivated olefins enabled by ligand-to-iron charge transfer and functional group migration strategies Mengqi Luo, Shibo Zhu, Jiawen Yin, Chao Yang, Lin Guo and Wujiong Xia Org. Chem. Front., 2024,11, 4748-4756 https://doi.org/10.1039/D4QO01025F
	Dearomative difunctionalization of arenes via highly selective radical relay reactions Ning Lei, Qian Zhang, Pan Tao, Cong Lu, Qian Lei and Ke Zheng Org. Chem. Front., 2024,11, 4654-4662 https://doi.org/10.1039/D4QO00964A
	Pd((R)-DTBM-SEGphos)Cl2-catalyzed kinetic resolution of tertiary propargylic alcohols Jie Wang, Wei-Feng Zheng, Yuling Li, Yin-Long Guo, Hui Qian and Shengming Ma Org. Chem. Front., 2024,11, 2477-2484 https://doi.org/10.1039/D4QO00082J
	Access to spiro-bicyclo[2.1.1]hexanes via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes Jia-Yi Su, Jian Zhang, Zhi-Yun Xin, Hao Li, Hanliang Zheng and Wei-Ping Deng Org. Chem. Front., 2024,11, 4539-4545 https://doi.org/10.1039/D4QO00511B
	Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis Yu-Heng Wang, Pan Hu, Xi-Rui Wang, Ke-Lan Xu, Qi-Lin Wang, Hui-Juan Wang and Xiong-Li Liu Org. Chem. Front., 2024,11, 1314-1321 https://doi.org/10.1039/D3QO01748F

We are proud to announce the three best covers of Organic Chemistry Frontiers in 2024! The awarded works were chosen by our readers through a worldwide vote. To learn more about the science behind the winning pieces, read for free the cover stories up until 03 February 2025.

	Photoredox catalyzed release of carbon-based radicals from 2-substituted-1,3-imidazolidines Adrián Luguera Ruiz, Elena Mariani, Stefano Protti and Maurizio Fagnoni Org. Chem. Front., 2024, 11, 661-667 https://doi.org/10.1039/D3QO01856C
	Photoredox/nickel dual-catalyzed deaminative cross-electrophile for allenylic alkylation with non-activated alkyl katritzky salts Zhao-Zhao Zhou, Xiao-Feng Zhai, Ke-Jian Xia, Xian-Rong Song, Haixin Ding, Wan-Fa Tian, Shu-Liang Zhang, Yong-Min Liang and Qiang Xiao Org. Chem. Front., 2024, 11, 5685-5694 https://doi.org/10.1039/D4QO00834K
	Catalytic intermolecular hydrofunctionalizations of ynamides Ying-Ying Zhao, Yu-Jing Jia and Yan-Cheng HuOrg. Chem. Front., 2024, 11, 2351-2374 https://doi.org/10.1039/D4QO00301B

Congratulations to the winners!

We would like to express our sincere appreciation for all the support and contribution from our authors, reviewers, and readers during 2024.

Looking forward to receiving your high-quality work in 2025.

Organic Chemistry Frontiers is delighted to announce the appointment of Professor Buddhadeb Chattopadhyay from Centre of Biomedical Research (CBMR), Lucknow, India as an Associate Editor. In his new role, Professor Chattopadhyay will contribute to the journal’s development through manuscripts management, strategic setting and more. Please join us in welcoming him!

Learn more about our new Associate Editor:

Buddhadeb obtained his B.Sc. (2001) in chemistry from the Burdwan University and M.Sc. (2003) in chemistry from Visva-Bharati University. In 2003, he left Visva-Bharati and enrolled in Kalyani University for his Ph.D. in the laboratories of Professor K. C. Majumdar. After postdoctoral research work around six years in the USA from 2009 to 2024 (University of Illinois at Chicago, USA and Michigan State University, East Lansing, USA), Buddhadeb started his independent research career at the Centre of Biomedical Research (CBMR), Lucknow, India, where he is currently holding the position of Associate Professor in the Department of Biological & Synthetic Chemistry.

Buddhadeb was the recipient of the Ramanujan Faculty award, DST Young Scientist Award, Thieme Chemistry Journal Award, SERB-STAR AWARD–2019 (Science and Technology Award for Research), SERB-TETRA AWARD–2022 (Technology Translation Award), Fellow of National Academy of Sciences (FNASc), and Fellow of the Royal Society of Chemistry (FRSC).

His research interest includes the catalyst/ligand engineering for the C–H bond activation/functionalization, especially C–H bond borylations of organic molecules and metal-nitrene/carbene chemistry via metalloradical catalysis. To find more about Buddhadeb and his research work, visit The Chattopadhyay Group.

Read some of our new AE’s research in the papers below:

	C–H borylation: a tool for molecular diversification Saikat Guria, Mirja Md Mahamudul Hassan and Buddhadeb Chattopadhyay* Org. Chem. Front., 2024,11, 929-953 10.1039/D3QO01931D
	An iron(ǁ)-based metalloradical system for intramolecular amination of C(sp2)–H and C(sp3)–H bonds: synthetic applications and mechanistic studies   Sandip Kumar Das, Subrata Das, Supratim Ghosh, Satyajit Roy, Monika Pareek, Brindaban Roy, Raghavan B. Sunoj* and Buddhadeb Chattopadhyay* Chem. Sci., 2022,13, 11817-11828 10.1039/D2SC03505G

Thermodynamic- and kinetic-controlled deprotonation of symmetric and asymmetric ketones is a well-known process that leads to the formation of enolates, one of the most important intermediate in organic chemistry. Regio-selective deprotonation assumes extreme importance, being critical to the success of organic reactions, when unsymmetrical carbonyl compounds such as ketones, having α-hydrogens in both sides, are taken into account. To the best of our knowledge, no studies have specifically reported on β-functionalized ketones in which regioselective formation of enolates could be less obvious and intuitive with respect to that observed in the most familiar α-functionalized analogues.

Figure 1. Chemical structure of ketones 1–6 involved in this study (A). Potential thermodynamic (4–6a) and kinetic enolates (4–6b) from the deprotonation of 4–6 using LHMDS (B).

Here we report a theoretical study at the DFT level of theory on a group of β-functionalized cyclic ketones 1–6 (Figure 1) to shed light on kinetic parameters (e.g., electronic effect and steric hindrance) and any other parameters (e.g., non-covalent interactions) related to the formation of kinetic and thermodynamic enolates through the use of hindered and strong bases, such as LHMDS and KHMDS. These bases have been taken into account as models to investigate the effect of counter cations (Li⁺ or K⁺) on the enolate formation process.

Surprisingly, “thermodynamic enolate” 4a was obtained as single product under kinetic conditions (THF, −78 °C) while ketone 5, gives “kinetic product” 5b as main enolate under same conditions with a regioselectivity of 70 : 30 over the “thermodynamic product” 5a. The unusual behavior reported in the literature for ketones 4 and 5 in the presence of LHMDS captured our attention and fed our curiosity.

Figure 2. Conformers and relative stability from Li-enolates from ketone 4. Relative stability for each Li-conformers is reported in kcal/mol in parentheses. Hydrogens have been hidden for better clarity.

A conformational study on the Li⁺@4 complex highlights the coordination ability of the functional group in β-positon (e.g. aldehyde group) and unveils its effect on the resulting enolate distribution (see Figure 2).  The lack of functional groups with coordination ability in 1–3 does not allow the double coordination of Li⁺ cation and consequently, no alteration of the enolate distribution is observed when (Me₃Si)₂^– was exchanged with LHMDS. The observed effect must be attributed to the coordination ability of the functional group (e.g. aldehyde in 4, cyano in 5 and nitro group in 6) and their directionality. Aldehyde and nitro group in 4 and 6, respectively, showed a superior directionality compared to cyano group in 5, leading to a higher stabilization of the relative TS for the presence of Li⁺ or K⁺ cations and consequently, higher regioselectivity towards “thermodynamic enolate” as experimentally reported (Table 1).

Table 1 Activation energy (E_a), ∆E_Ea and ∆∆E_Ea for ketones 4–6 in the presence of Li⁺ and K⁺.

On the other hand, the linear orientation of the cyano group (–C≡N) in 5 does not allow a proper coordination with the Li⁺ cation, showing a ∆E_Ea of 0.7 kcal/mol and leading us to suppose the presence of both enolates (5a and 5b) in the resulting solution (see Table 1 – Entries 5 and 6) as reported in literature. However, higher regioselectivity towards the “thermodynamic enolate” 5a is detected in presence of KHMDS where a ∆E_Ea of 4.9 kcal/mol is now observed (see Table 1 – Entries 7 and 8). This is rationalized by the better coordination between K⁺ cation and cyano group derived from the bigger size of the K⁺ cation with respect to the Li⁺ cation (Figure 3), highlighting how preliminary base selection (e.g., LHMDS vs. KHMDS) could strongly affect the resulting enolate distribution.

Figure 3. Comparison between thermodynamic enolates 4a (A), 5a (B) and 6a (C) coordinated to Li+ (left) and K+ (right).

We believe this work: (i) sheds light on the kinetic parameters that affect the regioselectivity in β-functionalized cyclic ketones, (ii) gives reasonable explanations for the unusual regioselectivity reported in the literature for some β-functionalized cyclic ketones such as 4 and 5, and (iii) could be a source of inspiration for future regioselective synthetic approaches and promotes the use of non-covalent interactions in the field of stereochemistry.

Corresponding author:

Emerging Investigator: Chuan He

Position          Associate Professor Postdoc          2013–2017  University of Cambridge Education       2008–2013  Wuhan University          Ph.D.                        2004–2008  Wuhan University          B.Sc. Group website        http://faculty.sustech.edu.cn/hec/en/ ORCID                    0000-0002-9983-7526

Read Chuan He’s Emerging Investigator Series article in Organic Chemistry Frontiers and learn more about him.

	Stereodivergent asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes
	Bo Yang,‡ Xingfa Tan,‡ Yicong Ge, Yingzi Li and Chuan He*
	We herein report an efficient one-pot strategy for the stereodivergent asymmetric synthesis of various P-atropisomeric Si-stereogenic monohydrosilanes with excellent stereoselectivity from dichlorosilanes.
	From the themed collection: OCF Emerging Investigator Series
	The article was first published on 23 Aug 2023
	Org. Chem. Front., 2023, Advance Article
	https://doi.org/10.1039/D3QO01084H

My research interests

10 Facts about me

Click to find out our Emerging Investigators and their work