Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans?
Organic Chemistry Frontiers Pub Date: 2022-04-08 DOI: 10.1039/D2QO00406B
Abstract
Organoselenium compounds are important structures in medicinal chemistry, materials chemistry and biochemistry. Many drugs contain heterocyclic skeletons. The selenation of pharmaceutical molecules is a promising way to discover new drugs. Herein, we introduced an electrochemical oxidative radical cascade cyclization of olefinic amides and diselenides without transition-metal catalysts and external oxidants. Various olefinic amides and diselenides were compatible, generating the desired products, more than 40 examples, in up to 94% yield. This selenocyclization reaction provided a facile method to construct C–Se and C–O bonds in one step.
Recommended Literature
- [1] Enabling chloride salts for thermal energy storage: implications of salt purity? J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. MayesRSC Adv., 2019,9, 25602-25608 10.1039/C9RA03133B
- [2] Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis? Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-GordonPhys. Chem. Chem. Phys., 2012,14, 15328-15339 10.1039/C2CP42522J
- [3] Excited-state proton-coupled electron transfer within ion pairs? Gerald J. Meyer,Leif Hammarstr?mChem. Sci., 2020,11, 3460-3473 10.1039/C9SC04941J
- [4] Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy? Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. ThieleChem. Commun., 2016,52, 12506-12509 10.1039/C6CC06771A
- [5] Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization. LarsBanko,AlfredLudwig 10.1021/acscombsci.0c00057
- [6] Excellent lithium ion storage property of porous MnCo2O4 nanorods? Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen FangRSC Adv., 2016,6, 23074-23084 10.1039/C5RA26176G
- [7] Examination of deposit in commercial diluted phosphoric acid Analyst, 1880,5, 146-147 10.1039/AN8800500146
- [8] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [9] Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors? Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon ChoJ. Mater. Chem. C, 2020,8, 1686-1696 10.1039/C9TC04955J
- [10] Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals? Shojiro Kimura,Tetsuro KusamotoChem. Commun., 2020,56, 11195-11198 10.1039/D0CC04830E
Journal Name:Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4