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Recent advance in the C-F bond functionalization of trifluoromethyl-containing compounds

Organofluorine compounds play an important role in pharmaceuticals, agrochemicals, and functional materials, due to their special chemical, physical and biological properties, such as increased electronegativity, hydrophobicity, bioavailability and metabolic stability. Therefore, great efforts have recently been devoted to the development of new methods for the synthesis of fluorinated compounds. Conventional strategies mainly focus on the selective introduction of fluorine atom or fluorine-containing moiety into organic molecules. Alternatively, the development of novel synthetic methodologies via the selective activation of C-F bond is of vital importance, which could allow for the synthesis of partially fluorinated synthetic intermediates from readily available polyfluorinated starting materials. The research of C-F bond activation is the most challenging task in organic synthesis, which has recently drawn increasing attention from chemists. In this review, we mainly focus on the C-F bond activation of CF3 groups for the synthesis of fluorinated compounds as well as discussion of their mechanisms(Scheme 1).

Scheme 1 The C-F bond functionalization of trifluoromethyl-containing compounds.

Due to the electron-deficient property, α-trifluoromethylstyrenes exhibit unique reactivities in their C-F bonds activation, mainly including three kinds of reactions (SN2′-type, SNV and ipso-substitution reactions, Scheme 2).

Scheme 2 Allylic and vinylic C-F bond activation in SN2’-type, SNV and ipso-sunstitution reactions

The cleavage of C-F bond in trifluoromethylated aromatic (Scheme 3) and alkyl compounds (Scheme 4) could be achieved through using transition metal complexes, main-group Lewis acids and base-conditions. An alternative strategy mainly relied on the single-electron transfer (SET) via Low-valent metals, irradiation with visible light.

Scheme 3 Photoredox-catalyzed defluoroalkylation of ArCF3 with unactivated alkenes.

Scheme 4 Pd-catalyzed defluorination/arylation reaction of α-trifluoromethyl ketones with aryl boronic acids.

Trifluoromethyl ketones (Scheme 5) and their corresponding diazo compounds (Scheme 6) , N‑tosylhydrazones (Scheme 7) have been utilized as the coupling partners in modern synthetic organic chemistry. Recently, the C-F bond cleavage of these compounds has also been reported through transition-metal catalysts.

Scheme 5 Cu-catalyzed reaction of trifluoromethylketones with aldehydes.

Scheme 6 Cu-catalyzed gem-difluoroolefination of diazo compounds.

Scheme 7 Cu-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes.

Although great progress has been made in this rapidly developing area, these reactions still suffer from some issues of the limitation of substrates and poor regioselectivity. To overcome these central challenges, it is more important to extend the substrate scope of the existing methodologies, especial trifluoromethylated alkyl compounds. Furthermore, the robust catalytic systems will be developed for the selective activation of a single C-F bond in CF3 groups.

 Guobing Yan

Zhejiang A&F University

Guobing Yan is a Professor in college of Jiyang at Zhejiang A&F University. He obtained B.Sc. degree from Jinggangshan Normal University, his M.Sc. degree from Suzhou University, and his Ph.D. degree from Tongji University in 2010. He spent two years in 2008 and 2009 as visiting student in professor Jianbo Wang’s laboratory at Peking University. In 2013, He joined Dr. Dong’s group at the University of Texas at Austin as a visiting professor. His current research interests focus on the transition-metal-catalyzed activation of inert chemical bonds and green synthetic chemistry. He is the author of 6 patents and more than 70 articles indexed by SCI.

 

Recent Advance in the C-F bond functionalization of trifluoromethyl-containing compounds

Guobing Yan, Kaiying Qiu and Ming Guo

https://doi.org/10.1039/D1QO00037C

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C(sp3)–H functionalization with isocyanides

Isocyanides have proven to be versatile building blocks in organic synthesis and medicinal chemistry due to their synthetic possibilities capable of reacting with electrophiles, nucleophiles and radicals. Multi-component reactions involving isocyanides have been well developed with the advantages of diverse skeletons of products, functional group compatibility, high chemo-, regio and stereoselectivities, and atom economy. With the continuous research on isocyanides, C(sp3)–H functionalization with isocyanides has made significant progresses with the advancement of mechanistic studies, new techniques and novel strategies in recent years. In this review, the group of Xu and coworkers of Shanghai University of China highlights the most recent advances of isocyanide chemistry in the C(sp3)–H functionalization since 2015 by elaborating the strategies of state-of-the-art synthetic routes. The synergistic combination of the isocyanide insertion and the C(sp3)–H bond activation offers a novel and efficient route to establish complicated reactions and provides an effective strategy for the synthesis of various nitrogen- and oxygen-containing compounds.

Figure 1.C(sp3)–H functionalization with isocyanides

Bin Xu received his bachelor’s degree from Shanghai University of Science and Technology in 1992. He conducted his PhD research with Professor Shengming Ma at Shanghai Institute of Organic Chemistry and completed his degree in 2000. After a two-year postdoctoral training at National Institutes of Health (NIH) as a Visiting Fellow (Mentor: Dr Kenneth A. Jacobson), he joined VivoQuest as a staff scientist (2002–2005). He began his independent academic career at Shanghai University in the end of 2005 as a Full Professor. His current research interests span the development of new methodology for nitrogen-containing heterocycles and their biological applications.

C(sp3)–H Functionalization with Isocyanides

Org. Chem. Front., 2021, Accepted Manuscript

https://pubs.rsc.org/en/content/articlelanding/2021/qo/d1qo00153a#!divAbstract

 

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Outstanding Reviewers for Organic Chemistry Frontiers in 2019

We would like to highlight the Outstanding Reviewers for Organic Chemistry Frontiers 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.

Dr Pablo Ballester, Institute of Chemical Research of Catalonia (ICIQ), ORCID: 0000-0001-8377-6610

Dr Ying-Chun Chen, Sichuan University, ORCID: 0000-0003-1902-0979

Prof Xuefeng Jiang East China Normal University, ORCID: 0000-0002-1849-6572

Dr Shukkoor Muhammed Kondengaden, Georgia State University

Prof Zhan Lu, Zhejiang Universitry, ORCID: 0000-0002-3069-079X

Dr Feng Shi, Jiangsu Normal University, ORCID: 0000-0003-3922-0708

Dr Qiuling Song, Huaqiao Univeristy, ORCID: 0000-0002-9836-8860

Dr Jie Wu, Fudan University, ORCID: 0000-0002-0967-6360

Dr Da-Gang Yu, Sichuan University, ORCID: 0000-0001-5888-1494

Dr Yonghui Zhang, Huazhong University of Science and Technology, ORCID: 0000-0002-7222-2142

We would also like to thank the Organic Chemistry Frontiers 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

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Welcome to Issue 13 of Organic Chemistry Frontiers in 2019

Welcome to issue 13 of Organic Chemistry Frontiers for 2019 ! The latest OrgChemFront issue is published online now.

 

The front cover story, Palladiumcatalyzed regioselective C–H alkynylation of indoles with bromoalkynes in water by Wanqing Wu and co-authors. The inside cover features a story on Trifluoromethyl-substituted selenium ylide: a broadly applicable electrophilic trifluoromethylating reagent by Hangming Ge and Qilong Shen .

 

 

 

 

 

 

 

Follow review type articles are included in current issue:

Developments towards synthesis of N-heterocycles from amidines via C–N/C–C bond formation
Wei Guo, Mingming Zhao, Wen Tan, Lvyin Zheng, Kailiang Tao and Xiaolin Fan

Org. Chem. Front., 2019,6, 2120-2141
https://doi.org/10.1039/C9QO00283A

 

Recent synthetic applications of α-amido sulfones as precursors of N-acylimino derivatives
Enrico Marcantoni, Alessandro Palmieri and Marino Petrini

Org. Chem. Front., 2019,6, 2142-2182
https://doi.org/10.1039/C9QO00196D

 

Metal-catalyzed radical-type transformation of unactivated alkyl halides with C–C bond formation
under photoinduced conditions
Shengqing Ye, Tianyi Xiang, Xiaofang Li and Jie Wu

Org. Chem. Front., 2019,6, 2183-2199
https://doi.org/10.1039/C9QO00272C

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Welcome to Issue 7 of Organic Chemistry Frontiers in 2019

Welcome to issue 7 of Organic Chemistry Frontiers for 2019 ! The latest OrgChemFront issue is published online now.

The front cover story, A concise approach for determining the relative configuration of H-7 and H-8 in 8,4′-oxyneolignans by 1H NMR spectroscopy, is contributed by  Pei-Cheng Zhang and co-authors.

The inside cover features a story on Guest-mediated chirality transfer in the host–guest complexes of an atropisomeric perylene bisimide cyclophane host by Frank Würthner and co-authors.

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9th Pacific Symposium on Radical Chemistry

OCF is very pleased to be sponsoring the “9th Pacific Symposium on Radical Chemistry (PSRC-9)” to be held at the Asilomar Conference Grounds in Pacific Grove, California, USA. The Symposium will be held from the 16th to the 21st of June 2019.

Register early for reduced fee by 1st April 2019!

The symposium will cover all aspects of free radical chemistry and will bring together industrial and academic chemists from all over the world to report their latest discoveries in the fields of synthetic radical reactions, radical polymerizations, mechanistic insights into important radical reactions, new radical-based functional molecules and materials, as well as all aspects of radicals impacting in biology and medicine. The scientific program of PSRC-9 will include plenary lectures and invited lectures as well as poster sessions.

Find out more about this conference from the official website!

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Hot Articles in November 2018

Organic Chemistry Frontiers is delighted to share with you the HOT article of November 2018!

You can access this publication for free till 31st  January 2019 by logging into your free Royal Society of Chemistry publishing personal account (http://pubs.rsc.org)

Cross-dehydrogenative alkynylation of sulfonamides and amides with terminal alkynes via Ir(III) catalysis
Guocai Wu, Wensen Ouyang, Qian Chen, Yanping Huo and Xianwei Li
Org. Chem. Front., 2018, Advance Article
http://dx.doi.org/10.1039/C8QO01105B

Direct conjugate additions using aryl and alkyl organic halides in air and water
Feng Zhou, Xiaoyun Hu, Wanying Zhang and Chao-Jun Li
Org. Chem. Front., 2018, Advance Article
http://dx.doi.org/10.1039/C8QO01141A

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Outstanding Reviewers for Organic Chemistry Frontiers in 2016

Following the success of Peer Review Week in September 2016 (dedicated to reviewer recognition) during which we published a list of our top reviewers, we are delighted to announce that we will continue to recognise the contribution that our reviewers make to the journal by announcing our Outstanding Reviewers each year.

We would like to highlight the Outstanding Reviewers for Organic Chemistry Frontiers in 2016, 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.

Professor Jie Wu, Fudan University

Professor Zhang-jie Shi, Fudan University

Professor Jin-Heng Li,  Hunan University

Professor Yuhong Zhang, Zhejiang University

Professor Shuanhu Gao, East China Normal University

Professor Itaru Nakamura, Tohoku University

Professor Xingwei Li, Dalian Institute of Chemical Physics

Professor Jianbo Wang, Peking University

Professor Qiuling Song, Huaqiao University

Professor Louis Fensterbank, Université Pierre et Marie Curie

We would also like to thank the Organic Chemistry Frontiers 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

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Hot Articles in January 2017

Organic Chemistry Frontiers is delighted to share with you the HOT articles of January 2017!

You can access these publications for free till 15th Mar 2017 by logging into your free Royal Society of Chemistry publishing personal account (http://pubs.rsc.org).

One-pot synthesis of fluorescent 2,4-dialkenylindoles by rhodium-catalyzed dual C–H functionalization
Hui Chen, Cong Lin, Chunhua Xiong, Zhanxiang Liu and Yuhong Zhang
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00755D, Research Article

Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives
Zhusheng Huang, Qingqing Chen, Xiuqin Yang, Yang Liu, Li Zhang, Tao Lu and Qingfa Zhou
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00775A, Research Article

5-Azadibenzo[a,g]corannulene
V. M. Tsefrikas, A. K. Greene and L. T. Scott
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00831C, Research Article

 

From tetrabenzoheptafulvalene to sp2 carbon nano-rings
Kwan Yin Cheung, Shuaijun Yang and Qian Miao
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00828C, Research Article

Iridium catalysts with modular axial-unfixed biphenyl phosphine–oxazoline ligands: asymmetric hydrogenation of α,β-unsaturated carboxylic acids
Qian Wang, Zongpeng Zhang, Caiyou Chen, Hailong Yang, Zhengyu Han, Xiu-Qin Dong and Xumu Zhang
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00677A, Research Article

 

Silver-catalyzed radical carbofluorination of unactivated alkenes with acetic acid in aqueous solution
He Chen, Lin Zhu and Chaozhong Li
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00854B, Research Article

 

Thiolate–palladium(IV) or sulfonium–palladate(0)? A theoretical study on the mechanism of palladium-catalyzed C–S bond formation reactions
Dongdong Xu, Xiaotian Qi, Meng Duan, Zhaoyuan Yu, Lei Zhu, Chunhui Shan, Xiaoyu Yue, Ruopeng Bai and Yu Lan
Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C6QO00841K, Research Article

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Welcome to Issue 7 of Organic Chemistry Frontiers in 2016

Welcome to issue 7 of Organic Chemistry Frontiers for 2016! The latest OrgChemFront issue is published online now

The front cover story, Magnetically separable nano-copper catalyzed unprecedented stereoselective synthesis of E-vinyl sulfones from tosylmethyl isocyanide and alkynes: TosMIC as a source of the sulfonyl group is contributed by Mandalaparthi Phanindrudu, Dipak Kumar Tiwari, B. Sridhar, Pravin R. Likhar and Dharmendra Kumar Tiwari. The inside cover features a story on Cu-catalyzed one-pot synthesis of fused oxazepinone derivatives via sp2 C–H and O–H cross-dehydrogenative coupling by Zeyuan Zhang, Zhen Dai, Xinkun Ma, Yihan Liu, Xiaojun Ma, Wanli Li and Chen Ma.



Mandalaparthi Phanindrudu, Dipak Kumar Tiwari, B. Sridhar, Pravin R. Likhar and Dharmendra Kumar Tiwari
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