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Synthesis 2019; 51(19): 3758-3764
DOI: 10.1055/s-0039-1690013
DOI: 10.1055/s-0039-1690013
paper
Metal-Free ipso-Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide
Aix-Marseille Université and the Centre National de la Recherche Scientifique (CNRS) are gratefully acknowledged for financial support.Further Information
Publication History
Received: 07 June 2019
Accepted after revision: 16 July 2019
Publication Date:
01 August 2019 (online)
Abstract
The first ipso-selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690013.
- Supporting Information
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References
- 1a Baquedano Y, Moreno E, Espuelas S, Nguewa P, Font M, Gutierrez KJ, Jiménez-Ruiz A, Palop JA, Sanmartín C. Eur. J. Med. Chem. 2014; 74: 116
- 1b Baquedano Y, Alcolea V, Toro MA, Gutierrez KJ, Nguewa P, Font M, Moreno E, Espuelas S, Jimenez-Ruiz A, Palop JA, Plano D, Sanmartín S. Antimicrob. Agents Chemother. 2016; 60: 3802
- 1c Martín-Montes Á, Plano D, Martín-Escolano R, Alcolea V, Díaz M, Pérez-Silanes S, Espuelas S, Moreno E, Marín C, Gutiérrez-Sánchez R, Sanmartín C, Sánchez-Moreno M. Antimicrob. Agents Chemother. 2017; 61: e02546-16
- 2a Facompre ND, El-Bayoumy K, Sun Y.-W, Pinto JT, Sinha R. Cancer Prev. Res. 2010; 3: 975
- 2b Plano D, Karelia DN, Pandey MK, Spallholz JE, Amin S, Sharma AK. J. Med. Chem. 2016; 59: 1946
- 2c Banerjee K, Padmavathi G, Bhattacherjee D, Saha S, Kunnumakkara AB, Bhabak KP. Org. Biomol. Chem. 2018; 16: 8769
- 3a Mukherjee N, Kundu D, Ranu BC. Adv. Synth. Catal. 2017; 359: 329
- 3b Maity P, Paroi B, Ranu BC. Org. Lett. 2017; 19: 5748
- 3c Maity P, Kundu D, Roy R, Ranu BC. Org. Lett. 2014; 16: 4122
- 3d Tran D, Haddad M, Ratovelomanana-Vidal V. Synthesis 2019; 51: 2532
- 4a Chen J, Wang T, Wang T, Lin A, Yao H, Xu J. Org. Chem. Front. 2017; 4: 130
- 4b Muniraj N, Dhineshkumar J, Prabhu KR. ChemistrySelect 2016; 5: 1033
- 4c Xiao J.-A, Li Y.-C, Cheng X.-L, Chen W.-Q, Cui J.-G, Huang Y.-M, Huang J, Xiao Q, Su W, Yang H. Org. Chem. Front. 2019; 6: 1967
- 4d Hoque IU, Chowdhury SR, Maity S. J. Org. Chem. 2019; 84: 3025
- 4e Feng C, Peng Y, Ding G, Li X, Cui C, Yan Y. Chem. Commun. 2018; 54: 13367
- 4f Abonia R, Gutierrez LF, Zwarycz AT, Correa Smits S, Laali KK. Heteroat. Chem. 2019; Article ID 1459681: DOI 10.1155/2019/1459681
- 5 Nikolaienko P, Rueping M. Chem. Eur. J. 2016; 22: 2620
- 6 Guan Y, Townsend SD. Org. Lett. 2017; 19: 5252
- 7 Zhu C, Falck JR. Adv. Synth. Catal. 2014; 356: 2395
- 8a Thiebes C, Surya PrakashG. K, Petasis NA, Olah GA. Synlett 1998; 141
- 8b Tramutola F, Chiummiento L, Funicello M, Lupattelli P. Tetrahedron Lett. 2015; 56: 1122
- 8c Cazorla C, Métay E, Andrioletti B, Lemaire M. Tetrahedron Lett. 2009; 50: 3936
- 9 Sun N, Zhang H, Mo W, Hu B, Shen Z, Hu X. Synlett 2013; 24: 1443
- 10a Kumar RU, Reddy KH. V, Swapna GS. K, Nageswar YV. D. Tetrahedron Lett. 2016; 57: 4138
- 10b Ren Y, Xu B, Zhong Z, Pittman CU, Zhou A. Org. Chem. Front. 2019; 6: 2023
- 11 Kachanov AV, Slabko OY, Baranova OV, Shilova EV, Kaminskii VA. Tetrahedron Lett. 2004; 45: 4461
- 12a Verneuil A. Ann. Chim. Phys. 1886; 41: 328
- 12b Aksnes O, Foss O. Acta Chem. Scand. 1954; 8: 1787
- 12c Hauge S. Acta Chem. Scand. 1971; 25: 3081
- 12d Burchell CJ, Kilian P, Slawin AM. Z, Woollins JD, Tersago K, Van Alsenoy C, Blockhuys F. Inorg. Chem. 2006; 45: 710
- 13a Obah Kosso AR, Broggi J, Redon S, Vanelle P. Synlett 2018; 29: 1215
- 13b Redon S, Obah Kosso AR, Broggi J, Vanelle P. Tetrahedron Lett. 2017; 58: 2771
- 13c Redon S, Kabri Y, Crozet MD, Vanelle P. Tetrahedron Lett. 2014; 55: 5052
- 13d Kabri Y, Crozet MD, Redon S, Vanelle P. Synthesis 2014; 46: 1613
- 14 Krief A, Dumont W, Delmotte C. Angew. Chem. Int. Ed. 2000; 39: 1669
- 15a Tiecco M, Testaferri L, Tingoli M, Chianelli D, Montanucci M. J. Org. Chem. 1983; 48: 4289
- 15b Singh D, Deobald AM, Camargo LR. S, Tabarelli G, Rodrigues OE. D, Braga AL. Org. Lett. 2010; 12: 3288
- 15c Soleiman-Beigi M, Yavarib I, Sadeghizadeh F. RSC Adv. 2015; 5: 87564
- 15d Barnes NA, Godfrey SM, Ollerenshaw RT. A, Khan RZ, Pritchard RG. Dalton Trans. 2012; 41: 14583
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First synthesis:
Crystal data: