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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Editorial

λ3-Iodane-Mediated Umpolung of Ketone and Enolate to Enolonium

Author(s): Keshaba Nanda Parida*

Volume 28, Issue 8, 2024

Published on: 05 April, 2024

Page: [573 - 575] Pages: 3

DOI: 10.2174/0113852728302831240315064301

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[1]
Seebach, D. Methods of reactivity umpolung. Angew. Chem. Int. Ed. Engl., 1979, 18(4), 239-258.
[http://dx.doi.org/10.1002/anie.197902393]
[2]
Seebach, D.; Corey, E.J. Generation and synthetic applications of 2-lithio-1,3-dithianes. J. Org. Chem., 1975, 40(2), 231-237.
[http://dx.doi.org/10.1021/jo00890a018]
[3]
Arava, S.; Kumar, J.N.; Maksymenko, S.; Iron, M.A.; Parida, K.N.; Fristrup, P.; Szpilman, A.M. Enolonium species-umpoled enolates. Angew. Chem. Int. Ed., 2017, 56(10), 2599-2603.
[http://dx.doi.org/10.1002/anie.201610274] [PMID: 28128488]
[4]
Kumar, R.; Nguyen, Q.H.; Um, T.W.; Shin, S. Recent progress in enolonium chemistry under metal‐free conditions. Chem. Rec., 2022, 22(1), e202100172.
[http://dx.doi.org/10.1002/tcr.202100172] [PMID: 34418282]
[5]
Spieß, P.; Shaaban, S.; Kaiser, D.; Maulide, N. New strategies for the functionalization of carbonyl derivatives via α-umpolung: From enolates to enolonium ions. Acc. Chem. Res., 2023, 56(12), 1634-1644.
[http://dx.doi.org/10.1021/acs.accounts.3c00171] [PMID: 37226674]
[6]
Parida, K.N.; Moorthy, J.N. λ3‐ and λ5‐iodanes: Substituent effects and pseudorotation/hypervalent twisting. Chemistry, 2023, 29(34), e202203997.
[http://dx.doi.org/10.1002/chem.202203997] [PMID: 36929780]
[7]
Parra, A. Chiral hypervalent iodines: Active players in asymmetric synthesis. Chem. Rev., 2019, 119(24), 12033-12088.
[http://dx.doi.org/10.1021/acs.chemrev.9b00338] [PMID: 31741377]
[8]
Singh, F.V.; Shetgaonkar, S.E.; Krishnan, M.; Wirth, T. Progress in organocatalysis with hypervalent iodine catalysts. Chem. Soc. Rev., 2022, 51(18), 8102-8139.
[http://dx.doi.org/10.1039/D2CS00206J] [PMID: 36063409]
[9]
Maksymenko, S.; Parida, K.N.; Pathe, G.K.; More, A.A.; Lipisa, Y.B.; Szpilman, A.M. Transition-metal-free intermolecular α-arylation of ketones via Enolonium species. Org. Lett., 2017, 19(23), 6312-6315.
[http://dx.doi.org/10.1021/acs.orglett.7b03064] [PMID: 29140710]
[10]
More, A.A.; Pathe, G.K.; Parida, K.N.; Maksymenko, S.; Lipisa, Y.B.; Szpilman, A.M. α-N-heteroarylation and α-azidation of ketones via Enolonium species. J. Org. Chem., 2018, 83(4), 2442-2447.
[http://dx.doi.org/10.1021/acs.joc.7b03058] [PMID: 29334466]
[11]
Shneider, O.S.; Pisarevsky, E.; Fristrup, P.; Szpilman, A.M. Oxidative umpolung α-alkylation of ketones. Org. Lett., 2015, 17(2), 282-285.
[http://dx.doi.org/10.1021/ol503384c] [PMID: 25562460]
[12]
Targel, T.A.; Kumar, J.N.; Shneider, O.S.; Bar, S.; Fridman, N.; Maximenko, S.; Szpilman, A.M. Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles. Org. Biomol. Chem., 2015, 13(9), 2546-2549.
[http://dx.doi.org/10.1039/C4OB02601B] [PMID: 25600653]
[13]
Mondal, S.; Chatterjee, N.; Maity, S. Recent developments on photochemical synthesis of 1,n‐dicarbonyls. Chemistry, 2023, 29(49), e202301147.
[http://dx.doi.org/10.1002/chem.202301147] [PMID: 37335758]
[14]
Lemmerer, M.; Schupp, M.; Kaiser, D.; Maulide, N. Synthetic approaches to 1,4-dicarbonyl compounds. Nat. Synth., 2022, 1(12), 923-935.
[http://dx.doi.org/10.1038/s44160-022-00179-1]
[15]
Parida, K.N.; Pathe, G.K.; Maksymenko, S.; Szpilman, A.M. Cross-coupling of dissimilar ketone enolates via Enolonium species to afford non-symmetrical 1,4-diketones. Beilstein J. Org. Chem., 2018, 14, 992-997.
[http://dx.doi.org/10.3762/bjoc.14.84] [PMID: 29977370]
[16]
Li, J.; Bauer, A.; Di Mauro, G.; Maulide, N. α‐arylation of carbonyl compounds through oxidative C−C bond activation. Angew. Chem. Int. Ed., 2019, 58(29), 9816-9819.
[http://dx.doi.org/10.1002/anie.201904899] [PMID: 31112360]
[17]
Bauer, A.; Di Mauro, G.; Li, J.; Maulide, N. An α‐cyclopropanation of carbonyl derivatives by oxidative umpolung. Angew. Chem. Int. Ed., 2020, 59(41), 18208-18212.
[http://dx.doi.org/10.1002/anie.202007439] [PMID: 32808419]
[18]
Arava, S.; Santra, S.K.; Pathe, G.K.; Kapanaiah, R.; Szpilman, A.M. Direct umpolung Morita–baylis–hillman like α‐functionalization of enones via Enolonium species. Angew. Chem., 2020, 132(35), 15283-15287.
[http://dx.doi.org/10.1002/ange.202005286]

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