Abstract
In the presence of I2, an acyloxyselenenylation of alkenes with diselenides and carboxylic acids is developed. This metal-free iodine-mediated acyloxyselenenylation proceeds efficiently under mild reaction conditions, affording a series of 2-acyloxy-1-selenides with high regioselectivity and in moderate to good yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Back TG (1987) Preparative uses of organoselenium and organotellurium compounds. In: Patai S, Rappoport Z (eds) The chemistry of organic selenium and tellurium compounds, 2nd edn. Wiley, Chichester
Bosman C, D’Annibale A, Resta S, Trogolo C (1994) Oxidation of diphenyl diselenide with ceric ammonium nitrate: a novel route for functionalization of olefins. Tetrahedron Lett 35:6525–6528. https://doi.org/10.1016/S0040-4039(00)78263-3
Das JP, Roy UK, Roy S (2005) Synthesis of alkynyl and vinyl selenides via selenodecarboxylation of arylpropiolic and cinnamic acids. Organometallics 24:6136–6140. https://doi.org/10.1021/om050504b
Huang ZZ, Huang X, Huang YZ (1995) Synthesis of acyl(phenylselanyl)-methylidene(triphenyl)-λ5-arsanes and their Wittig-type reactions. J Chem Soc Perkin Trans 1:95–96. https://doi.org/10.1039/P19950000095
Masato Y, Naomi S, Nobumasa K (1989) Novel method for electrophilic selenenylation using diselenide with nitrobenzenesulfonyl peroxide. Chem Lett 18:1433–1436. https://doi.org/10.1246/cl.1989.1433
Masato Y, Shuichi S, Kyoko K, Takashi S, Nobumasa K (1991) Oxidative cleavage of diselenide by m-mitrobenzenesulfonyl peroxide. Novel method for the electrophilic benzeneselenenylations of olefins and aromatic rings. Bull Chem Soc Jpn 64:416–422. https://doi.org/10.1246/bcsj.64.416
Mironov YV, Sherman AA, Nifantiev NE (2004) Homogeneous azidophenylselenylation of glycals using TMSN3–Ph2Se2–PhI(OAc)2. Tetrahedron Lett 45:9107–9110. https://doi.org/10.1016/j.tetlet.2004.10.022
Muangkaew C, Katrun P, Kanchanarugee P, Pohmakotr M, Reutrakul V, Soorukram D, Jaipetch T, Kuhakarn C (2013) PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: facile synthesis of β-acetoxysulfides. Tetrahedron 69:8847–8856. https://doi.org/10.1016/j.tet.2013.08.018
Nicolaou KC, Seitz SP, Sipio WJ, Blount JF (1979) Phenylseleno- and phenylsulfenolactonizations. Two highly efficient and synthetically useful cyclization procedures. J Am Chem Soc 101:3884–3893. https://doi.org/10.1021/ja00508a028
Paulmier C (1986) Selenium reagents and intermediates in organic synthesis, Chap 2. Pergamon Press, Oxford
Shi M, Wang B-Y, Li J (2005) Reactions of gem-aryl-disubstituted methylenecyclopropanes with diaryl diselenide in the presence of iodosobenzene diacetate. Eur J Org Chem 2005:759–765. https://doi.org/10.1002/ejoc.200400644
Shi HW, Yu C, Zhu M, Yan J (2015a) Novel and convenient acetoxyselenenylation of alkenes catalyzed by potassium iodide. J Organomet Chem 776:117–122. https://doi.org/10.1016/j.jorganchem.2014.10.025
Shi HW, Yu C, Yan J (2015b) Potassium bromide or sodium chloride catalyzed acetoxyselenenylation of alkenes with diselenides and mCPBA. Chin Chem Lett 26:1117–1120. https://doi.org/10.1016/j.cclet.2015.05.029
Taniguchi N (2006) Copper-catalyzed 1,2-hydroxysulfenylation of alkene using disulfide via cleavage of the S–S bond. J Org Chem 71:7874–7876. https://doi.org/10.1021/jo060834l
Tiecco M, Testaferri L, Tingoli M, Chianelli D, Bartoli D (1989) The reaction of diphenyl diselenide with peroxydisulphate ions in methanol a convenient procedure to effect the methoxyselenenylation of alkenes. Tetrahedron Lett 30:1417–1420. https://doi.org/10.1016/S0040-4039(00)99480-2
Tiecco M, Testaferri L, Tingoli M, Bartoli D, Balducci R (1990) Ring-closure reactions initiated by the peroxydisulfate ion oxidation of diphenyl diselenide. J Org Chem 55:429–434. https://doi.org/10.1021/jo00289a010
Tiecco M, Testaferri L, Temperini A, Bagnoli L, Marini F, Santi C (1998) Iodosobenzene diacetate and diphenyl diselenide: an electrophilic selenenylating agent of double bonds. Synth Commun 28:1769–1778. https://doi.org/10.1080/00397919808007007
Tiecco M, Testaferri L, Temperini A, Bagnoli L, Marini F, Santi C (2001) Oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). A new method for the electrophilic phenylselenenylation of alkenes under mild conditions. Synlett 11:1767–1771. https://doi.org/10.1055/s-2001-18091
Tingoli M, Tiecco M, Chianelli D, Balducci R, Temperini A (1991) Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process. J Org Chem 56:6809–6813. https://doi.org/10.1021/jo00024a020
Tingoli M, Tiecco M, Testaferri L, Balducci R (1993) Reactions of terminal alkynes with iodobenzene diacetate and diphenyl diselenide: synthesis of phenyl alkynyl selenides. Synlett 1993:211–212. https://doi.org/10.1055/s-1993-22405
Tingoli M, Tiecco M, Testaferri L, Temperini A (1994) Substituted azides from selenium-promoted deselenenylation of azido selenides. Glycosylation reactions of protected 2-azido-2-deoxy-1-selenoglycopyranoses. J Chem Soc Chem Commun 1883–1884. https://doi.org/10.1039/C39940001883
Tingoli M, Diana R, Panunzi B (2006) N-Phenylselenosaccharin (NPSSac): a new electrophilic selenium-containing reagent. Tetrahedron Lett 47:7529–7531. https://doi.org/10.1016/j.tetlet.2006.08.068
Trost BM, Ochiai M, McDougal PG (1978) Hydroxysulfenylation of olefins. An olefin cleavage with functional group differentiation. J Am Chem Soc 100:7103–7106. https://doi.org/10.1021/ja00490a072
Wang XL, Li HJ, Zhu M, Yan J (2017) Convenient iodine-mediated aminoselenation of alkenes using benzotriazoles as nitrogen sources. RSC Adv 7:15709–15714. https://doi.org/10.1039/C6RA27202A
Wirth T (2000) Organoselenium chemistry in stereoselective reactions. Angew Chem Int Ed 39:3740–3749. https://doi.org/10.1002/1521-3773(20001103)39:21
Yu L, Chen B, Huang X (2007) Multicomponent reactions of allenes, diaryl diselenides, and nucleophiles in the presence of iodosobenzene diacetate: direct synthesis of 3-functionalized-2-arylselenyl substituted allyl derivatives. Tetrahedron Lett 48:925–927. https://doi.org/10.1016/j.tetlet.2006.12.026
Zhang YK, Wu SX, Yan J (2017) PhI catalyzed acetoxyselenylation and formyloxyselenylation of alkenes. Helv Chim Acta 100:e1600306. https://doi.org/10.1002/hlca.210600306
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, X., Wang, J., Li, H. et al. Iodine-mediated acyloxyselenenylation of alkenes. Chem. Pap. 72, 2745–2752 (2018). https://doi.org/10.1007/s11696-018-0496-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-018-0496-5