Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
- Corresponding author: Yan Jie, jieyan87@zjut.edu.cn
Citation:
Wu Si-Xue, Zhang Yi-Kun, Shi Hong-Wei, Yan Jie. Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions[J]. Chinese Chemical Letters,
;2016, 27(9): 1519-1522.
doi:
10.1016/j.cclet.2016.03.024
Finkbeiner P., Nachtsheim B.J.. Iodine in modern oxidation catalysis[J]. Synthesis, 2013,45:979-999. doi: 10.1055/s-00000084
Zhao J., Li P., Xia C.. Direct N-acylation of azoles via a metal-free catalyzed oxidative cross-coupling strategy[J]. Chem. Commun., 2014,50:4751-4754. doi: 10.1039/c4cc01587h
Guo S., Yu J.T., Dai Q.. The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols[J]. Chem. Commun., 2014,50:6240-6242. doi: 10.1039/c4cc01652a
Wu X.F., Gong J.L., Qi X.. A powerful combination:recent achievements on using TBAI and TBHP as oxidation system[J]. Org. Biomol. Chem., 2014,12:5807-5817. doi: 10.1039/C4OB00276H
Jia Z., Nagano T., Li X.. Iodide-ion-catalyzed carbon-carbon bond-forming cross-dehydrogenative coupling for the synthesis of indole derivatives[J]. Eur. J. Org. Chem., 2013:858-861.
Zeng L.Y., Yi W.B., Cai C.. Three-component domino synthesis of 2-arylquinazoline-4-amines in one pot by activating an sp3 C-H bond in a nonmetal catalytic oxidation system[J]. Eur. J. Org. Chem., 2012:559-566.
Froehr T., Sindlinger C.P., Kloeckner U.. A metal-free amination of benzoxazoles-the first example of an iodide-catalyzed oxidative amination of heteroarenes[J]. Org. Lett., 2011,13:3754-3757. doi: 10.1021/ol201439t
Lamani M., Prabhu K.R.. Iodine-catalyzed amination of benzoxazoles:a metal-free route to 2-aminobenzoxazoles under mild conditions[J]. J. Org. Chem., 2011,76:7938-7944. doi: 10.1021/jo201402a
Reddy K.R., Maheswari C.U., Venkateshwar M.. Oxidative amidation of aldehydes and alcohols with primary amines catalyzed by KI-TBHP[J]. Eur. J. Org. Chem., 2008:3619-3622.
Liotta D.. New organoselenium methodology[J]. Acc. Chem. Res., 1984,17:28-34. doi: 10.1021/ar00097a005
Tang S., Wu Y., Liao W.. Revealing the metal-like behavior of iodine:an iodide-catalysed radical oxidative alkenylation[J]. Chem. Commun., 2014,50:4496-4499. doi: 10.1039/c4cc00644e
Lin Y.M., Lu G.P., Cai C.. Odorless, one-pot regio-and stereoselective iodothiolation of alkynes with sodium arenesulfinates under metal-free conditions in water[J]. Org. Lett., 2015,17:3310-3313. doi: 10.1021/acs.orglett.5b01488
Kariya A., Yamaguchi T., Nobuta T.. Molecular-iodine-catalyzed aerobic oxidative synthesis of β-hydroxy sulfones from alkenes[J]. RSC Adv., 2014,4:13191-13194. doi: 10.1039/c3ra47863g
Katrun P., Hongthong S., Hlekhlai S.. Iodine-PPh3-mediated C3-sulfenylation of indoles with sodium sulfinates[J]. RSC Adv., 2014,4:18933-18938. doi: 10.1039/c4ra02607a
Gao W.C., Zhao J.J., Hu F.. I2-mediated sulfonylation and Na2SO3-mediated deacylation:a general protocol for the synthesis of β-keto sulfones and bdicarbonyl sulfones[J]. RSC Adv., 2015,5:25222-25228. doi: 10.1039/C5RA03826J
Katrun P., Mueangkaew C., Pohmakotr M.. Regioselective C2 sulfonylation of indoles mediated by molecular iodine[J]. J. Org. Chem., 2014,79:1778-1785. doi: 10.1021/jo402831k
Xiao F.H., Chen H., Xie H.. Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates[J]. Org. Lett., 2014,16:50-53. doi: 10.1021/ol402987u
Xiao F.H., Xie H., W. S.. Iodine-catalyzed regioselective sulfenylation of indoles with sodium sulfinates[J]. Adv. Synth. Catal., 2014,356:364-368. doi: 10.1002/adsc.201300773
Yang K., Ke M., Lin Y.G.. Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature[J]. Green Chem., 2015,17:1395-1399. doi: 10.1039/C4GC02236J
Pan X.J., Gao J., Liu J.. Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature[J]. Green Chem., 2015,17:1400-1403. doi: 10.1039/C4GC02115K
Wei W., Liu C.L., Yang D.S.. Metal-free direct construction of sulfonamides via iodine-mediated coupling reaction of sodium sulfinates and amines at room temperature[J]. Adv. Synth. Catal., 2015,357:987-992. doi: 10.1002/adsc.v357.5
Chonchanok B., Danupat B., Sirilata Y.. Iodine-catalyzed oxidative amination of sodium sulfinates:a convenient approach to the synthesis of sulfonamides under mild conditions[J]. Eur. J. Org. Chem., 2015:1575-1582.
Katritzky A.R., Zhang G., Wu J.. 1-Phenylsulfonylbenzotriazole:a novel and convenient reagent for the preparation of benzenesulfonamides and aryl benzenesulfonates[J]. Synth. Commun., 1999,24:205-216.
Katritzky A.R., He H.Y., Suzuki K.. N-Acylbenzotriazoles:neutral acylating reagents for the preparation of primary, secondary, and tertiary amides[J]. J. Org. Chem., 2000,65:8210-8213. doi: 10.1021/jo000792f
Katritzky A.R., Shobana N., Pernak J.. Sulfonyl derivatives of benzotriazole:Part 1. A novel approach to the activation of carboxylic acids[J]. Tetrahedron, 1992,48:7817-7822. doi: 10.1016/S0040-4020(01)80459-2
Katritzky A.R., Abdel-Fattah A.A.A., Vakulenko A.V.. N-Sulfonylbenzotriazoles as advantageous reagents for C-sulfonylation[J]. J. Org. Chem., 2005,70:9191-9197. doi: 10.1021/jo051157i
Hergert L.Y., Nieto M.J., Becerra M.C.. Synthesis of N-benzenesulfonylbenzotriazole derivatives, and evaluation of their antimicrobial activity[J]. Lett. Drug Des. Discov., 2008,5:313-318. doi: 10.2174/157018008784912108
Soundararajan R., R. T.. Balasubramanian, Novel synthesis of potential biocides[J]. Chem. Ind. (Lond.), 1985,392.
Neikova N., Simov D., Karparov A.. 1-(Benzenesulfonyl)benzotriazoles and intermediate products with antiviral activity, Farmatsiya (Sofia[J]. Bulgaria), 1981,31:48-53.
Purygin P.P., Ivanov I.P., Laletina Z.P.. Synthesis and biological activity of N, N'-sulfuryldibenzotriazole[J]. Khim. Farm. Zh., 1983,17:792-793.
Katritzky A.R., Rodriguez-Garcia V., Nair S.K.. A general and efficient synthesis of sulfonylbenzotriazoles from N-chlorobenzotriazole and sulfinic acid salts[J]. J. Org. Chem., 2004,69:1849-1852. doi: 10.1021/jo035515y
Truce W.E., Wolf G.C.. Adducts ofsulfonyl iodides with acetylenes[J]. J. Org. Chem., 1971,36:1727-1732. doi: 10.1021/jo00812a001
Correa C.M.M.D.S., Waters W.A.. Reactions of the free toluene-p-sulphonyl radical. Part I. Diagnostic reactions of free radicals[J]. J. Chem. Soc. C, 1968:1874-1879.
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