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      Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

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          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Summary

          Cross-coupling reactions between aryl iodide and nucleophiles have been well developed. Iodoniums equipped with a reactive C-I(III) bond accelerate cross-coupling reactions of aryl iodide. Among them, cyclic diaryliodoniums are more atom economical; however; they are often in the trap of metal reliance and encounter regioselectivity issues. Now, we have developed a series of highly reactive cyclic monoaryl-vinyl iodoniums that can be tuned to construct C-N, C-O, and C-C bonds without metal catalysis. Under promotion of triethylamine, coupling reactions with aniline, phenol, aromatic acid, and indole proceed rapidly and regioselectively at room temperature. The carbene species is conceptualized as a key intermediate in our mechanism model. Furthermore, the coupling products enable diversity-oriented synthesis strategy to further build up a chemical library of diverse heterocyclic fragments that are in demand in the drug discovery field. Our current work provides a deep insight into the synthetic application of these highly reactive cyclic iodoniums.

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          Highlights

          • Highly reactive cyclic monoaryl-vinyl iodoniums were designed and synthesized

          • Coupling reactions with various nucleophiles took place in metal-free condition

          • A mechanism involving carbene species from cyclic vinyl iodoniums was hypothesized

          • Flexible transformations to build up chemical library through DOS strategy

          Abstract

          Chemistry; Catalysis; Organic Chemistry; Organic Synthesis

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          Most cited references 48

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          Bond formations between two nucleophiles: transition metal catalyzed oxidative cross-coupling reactions.

           Chao Liu,  Hua Zhang,  Wei Shi (2011)
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            Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

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              Diaryliodonium Salts: A Journey from Obscurity to Fame

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                Author and article information

                Contributors
                Journal
                iScience
                iScience
                iScience
                Elsevier
                2589-0042
                23 June 2020
                24 July 2020
                23 June 2020
                : 23
                : 7
                Affiliations
                [1 ]State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Sun Yat-sen University Cancer Center, 651 Dongfeng East Road, Guangzhou 510060, China
                [2 ]Berhampore Girl's College, Berhampore, Murshidabad, West Bengal 742101, India
                [3 ]Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, China
                [4 ]School of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, China
                Author notes
                []Corresponding author huangpeng@ 123456sysucc.org.cn
                [∗∗ ]Corresponding author wenshj@ 123456sysucc.org.cn
                [5]

                Lead Contact

                Article
                S2589-0042(20)30494-6 101307
                10.1016/j.isci.2020.101307
                7338778
                32634743
                © 2020 The Authors

                This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

                Categories
                Article

                organic synthesis, organic chemistry, catalysis, chemistry

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