Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(06): 1095-1102DOI: 10.1055/s-0040-1707317 paper Visible-Light-Driven Z-Selective Reaction of Methyl Ketones with DMSO: A Mild Synthetic Approach to Methylthio-Substituted 1,4-Enedione Promoted by Selectfluor™ Gaurav K. Rastogi a Department of Applied Sciences, GUIST, Gauhati University, Guwahati-781014, Assam, India eMail: mohitdd.deb@gmail.com eMail: baruah.pranjal@gmail.com b A Department of Applied Organic Chemistry, CSIR-NEIST, Jorhat-785006, Assam, India , Mohit L. Deb∗ a Department of Applied Sciences, GUIST, Gauhati University, Guwahati-781014, Assam, India eMail: mohitdd.deb@gmail.com eMail: baruah.pranjal@gmail.com , Pranjal K. Baruah∗ a Department of Applied Sciences, GUIST, Gauhati University, Guwahati-781014, Assam, India eMail: mohitdd.deb@gmail.com eMail: baruah.pranjal@gmail.com › Institutsangaben Artikel empfehlen Abstract Alle Artikel dieser Rubrik Abstract Here we disclose a simple, visible-light-driven Z-selective synthesis of methylthio-substituted 1,4-enedione in a single step promoted by Selectfluor. Dimethyl sulfoxide is used as both the ‘thio’ source and the solvent. Molecular iodine and potassium persulfate are used as catalyst and oxidant, respectively. White light (CFL-30W) is used as the light source. The proposed mechanism involves a Kornblum reaction followed by aldol reaction. Key words Key wordsvisible light - Selectfluor - 1,4-enedione - Z-selective Volltext Referenzen References 1a Roslin S, Odell LR. Eur. J. Org. Chem. 2017; 1993 1b Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102 1c Teplý F. Collect. Czech. Chem. Commun. 2011; 76: 859 1d Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617 1e Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785 1f Ravelli D, Dondi D, Fagnoni M, Albini A. Chem. Soc. Rev. 2009; 38: 1999 1g Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527 1h Srivastava V, Singh PK, Srivastava A, Singh PP. RSC Adv. 2020; 10: 20046 2a Chen J, Cen J, Xu X, Li X. Catal. Sci. Technol. 2016; 6: 349 2b Shi L, Xia W. Chem. Soc. Rev. 2012; 41: 7687 2c Rauch M, Schmidt S, Arends IW. C. E, Oppelt K, Kara S, Hollmann F. Green Chem. 2017; 19: 376 2d Xuan J, Feng Z.-J, Duan S.-W, Xiao W.-J. RSC Adv. 2012; 2: 4065 2e Sudo Y, Yamaguchi E, Itoh A. Org. Lett. 2017; 19: 1610 2f Hu J, Wang J, Nguyen TH, Zheng N. Beilstein J. Org. Chem. 2013; 9: 1977 2g Nicholls TP, Leonori D, Bissember AC. Nat. Prod. Rep. 2016; 33: 1248 2h Stephenson CR. J, Yoon TP, MacMillan DW. C, Douglas JJ. The Application of Visible-Light-Mediated Reactions to the Synthesis of Pharmaceutical Compounds . Wiley-VCH; Weinheim: 2018 3a Condie AG, González-Gómez JC, Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464 3b Wang C.-M, Xia P.-J, Xiao J.-A, Li J, Xiang H.-Y, Chen X.-Q, Yang H. J. Org. Chem. 2017; 82: 3895 3c Borra S, Chandrasekhar D, Adhikary S, Rasala S, Gokulnath S, Maurya RA. J. Org. Chem. 2017; 82: 2249 4a Rogers DA, Brown RG, Brandeburg ZC, Ko EY, Hopkins MD, LeBlanc G, Lamar AA. ACS Omega 2018; 3: 12868 4b Bogdos MK, Pinard E, Murphy JA. Beilstein J. Org. Chem. 2018; 14: 2035 4c Xia J.-B, Zhu C, Chen C. J. Am. Chem. Soc. 2013; 135: 17494 4d Mi X, Kong Y, Yang H, Zhang J, Pi C, Cui X. Eur. J. Org. Chem. 2020; 1019 5a Hari DP, König B. Chem. Commun. 2014; 50: 6688 5b Hari DP, König B. Org. Lett. 2011; 13: 3852 5c Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951 5d Majek M, Filace F, von Wangelin AJ. Beilstein J. Org. Chem. 2014; 10: 981 5e Sharma S, Sharma A. Org. Biomol. Chem. 2019; 17: 4384 5f Borpatra PJ, Deb ML, Baruah PK. Tetrahedron Lett. 2017; 58: 4006 5g Vila C, Lau J, Rueping M. Beilstein J. Org. Chem. 2014; 10: 1233 6a Yin F, Wang Z, Li Z, Li C. J. Am. Chem. Soc. 2012; 134: 10401 6b Pitts CR, Bloom S, Woltornist R, Auvenshine DJ, Ryzhkov LR, Siegler MA, Lectka T. J. Am. Chem. Soc. 2014; 136: 9780 6c Zhang Q, Yin X.-S, Chen K, Zhang S.-Q, Shi B.-F. J. Am. Chem. Soc. 2015; 137: 8219 6d Xie L.-Y, Qu J, Peng S, Liu K.-J, Wang Z, Ding M.-H, Wang Y, Cao Z, He W.-M. Green Chem. 2018; 20: 760 6e Yadav JS, Reddy BV. S, Sunitha V, Reddy KS. Adv. Synth. Catal. 2003; 345: 1203 7a Zhou J, Zou Y, Zhou P, Chen Z, Li J. Org. Chem. Front. 2019; 6: 1594 7b Mei H, Liu J, Pajkert R, Röschenthaler G.-V, Han J. Org. Biomol. Chem. 2020; 18: 3761 7c Hu J, Zhou G, Tian Y, Zhao X. Org. Biomol. Chem. 2019; 17: 6342 7d Yuan J.-W, Zhu J.-L, Li B, Yang L.-Y, Mao P, Zhang S.-R, Li Y.-C, Qu L.-B. Org. Biomol. Chem. 2019; 17: 10178 7e He G, Li Y, Yu Z, Chen Z, Tang Y, Song G, Loh T.-P. Org. Chem. Front. 2019; 6: 3644 7f Yang K, Song M, Ali AI. M, Mudassir SM, Ge H. Chem. Asian J. 2020; 15: 729 8a Niu L, Liu J, Liang X.-A, Wang S, Lei A. Nat. Commun. 2019; 10: 467 8b Liang X.-A, Niu L, Wang S, Liu J, Lei A. Org. Lett. 2019; 21: 2441 8c Zhao H, Jin J. Org. Lett. 2019; 21: 6179 8d Wang S, Liu J, Niu L, Yi H, Chiang C.-W, Lei A. J. Photochem. Photobiol., A 2018; 355: 120 9a Lv F, Xu M, Deng Z, de Voogd NJ, van Soest RW. M, Proksch P, Lin W. J. Nat. Prod. 2008; 71: 1738 9b Salvá J, Faulkner DJ. J. Org. Chem. 1990; 55: 1941 9c Cai P, Kong F, Ruppen ME, Glasier G, Carter GT. J. Nat. Prod. 2005; 68: 1736 10a Danishefsky S, Kahn M. Tetrahedron Lett. 1981; 22: 489 10b Allen JG, Danishefsky SJ. J. Am. Chem. Soc. 2001; 123: 351 10c Ballini R, Bosica G. Tetrahedron 1995; 51: 4213 10d Ballini R, Bosica G, Fiorini D, Gil MV, Petrini M. Org. Lett. 2001; 3: 1265 10e Lenz GR. J. Org. Chem. 1979; 44: 1597 11a Asta C, Conrad J, Mika S, Beifuss U. Green Chem. 2011; 13: 3066 11b Eberhardt MK. J. Org. Chem. 1993; 58: 472 11c Bailey PS, Hwang HH. J. Org. Chem. 1985; 50: 1779 11d Nandakumar M, Sivasakthikumaran R, Mohanakrishnan AK. Eur. J. Org. Chem. 2012; 3647 11e Li S.-Y, Wang X.-B, Jiang N, Kong L.-Y. Eur. J. Org. Chem. 2014; 8035 11f Prakash O, Batra A, Chaudhri V, Prakash R. Tetrahedron Lett. 2005; 46: 2877 11g Crone B, Kirsch SF. Chem. Commun. 2006; 764 11h Baratta W, Zotto AD, Rigo P. Chem. Commun. 1997; 2163 12a Yin G, Zhou B, Meng X, Wu A, Pan Y. Org. Lett. 2006; 8: 2245 12b Rastogi GK, Deka B, Deb ML, Baruah PK. Eur. J. Org. Chem. 2020; 424 13a Ji X, Li D, Zhou X, Huang H, Deng G.-J. Green Chem. 2017; 19: 619 13b Zhang X, Wang L. Green Chem. 2012; 14: 2141 13c Deb ML, Saikia B, Rastogi GK, Baruah PK. ChemistrySelect 2018; 3: 1693 13d Gao Q, Zhang J, Wu X, Liu S, Wu A. Org. Lett. 2015; 17: 134 13e Wu J.-C, Song R.-J, Wang Z.-Q, Huang X.-C, Xie Y.-X, Li J.-H. Angew. Chem. Int. Ed. 2012; 51: 3453 13f Wu X, Gao Q, Geng X, Zhang J, Wu Y.-D, Wu A.-X. Org. Lett. 2016; 18: 2507 13g Rastogi GK, Saikia B, Pahari P, Deb ML, Baruah PK. Tetrahedron Lett. 2019; 60: 1189 14a Noikham M, Yotphan S. Eur. J. Org. Chem. 2019; 2759 14b Shukla G, Srivastava A, Nagaraju A, Raghuvanshi K, Singh MS. Adv. Synth. Catal. 2015; 357: 3969 14c Mao X, Ni J, Xu B, Ding C. Org. Chem. Front. 2020; 7: 350 14d Jana A, Panday AK, Mishra R, Parvin T, Choudhury LH. ChemistrySelect 2017; 2: 9420 15a Sun ZY, Botros E, Su AD, Kim Y, Wang EJ, Baturay NZ, Kwon CH. J. Med. Chem. 2000; 43: 4160 15b Wang YG, Chackalamannil S, Hu ZY, Clader JW, Greenlee W, Billard W, Binch H, Crosby G, Ruperto V, Duffy RA, McQuade R, Lachowicz JE. Bioorg. Med. Chem. Lett. 2000; 10: 2247 15c Otzen T, Wempe EG, Kunz B, Bartels R, Lehwark-Yvetot G, Hansel W, Schaper K.-J, Seydel JK. J. Med. Chem. 2004; 47: 240 15d Nielsen SF, Nielsen EO, Olsen GM, Liljefors T, Peters DJ. Med. Chem. 2000; 43: 2217 15e Eichman CC, Stambuli JP. Molecules 2011; 16: 590 15f Haq K, Ali M. Biologically Active Sulphur Compounds of Plant Origin. Springer; Dordrecht: 2003 16a Tashrifi Z, Khanaposhtani MM, Larijani B, Mahdavi M. Adv. Synth. Catal. 2020; 362: 65 16b Jones-Mensah E, Karki M, Magolan J. Synthesis 2016; 48: 1421 16c Wua X.-F, Natte K. Adv. Synth. Catal. 2016; 358: 336 16d Xu Y, Cong T, Liu P, Sun P. Org. Biomol. Chem. 2015; 13: 9742 17a Cui X, Liu X, Wang X, Tian W, Wei D, Huang G. ChemistrySelect 2017; 2: 8607 17b Wu Y.-H, Wang N.-X, Zhang T, Yan Z, Xu B.-C, Inoa J, Xing Y. Adv. Synth. Catal. 2019; 361: 3008 17c Sharma P, Rohilla S, Jain N. J. Org. Chem. 2015; 80: 4116 17d Gao Q, Liu S, Wu X, Wu A. Tetrahedron Lett. 2014; 55: 6403 17e Gao X, Pan X, Gao J, Jiang H, Yuan G, Li Y. Org. Lett. 2015; 17: 1038 17f Zhao W, Xie P, Bian Z, Zhou A, Ge H, Zhang M, Ding Y, Zheng L. J. Org. Chem. 2015; 80: 9167 18a Froehr T, Sindlinger CP, Kloeckner U, Finkbeiner P, Nachtsheim BJ. Org. Lett. 2011; 13: 3754 18b Kloeckner U, Weckenmann NM, Nachtsheim BJ. Synlett 2012; 23: 97 18c Yan Y, Zhang Y, Zha Z, Wang Z. Org. Lett. 2013; 15: 2274 18d Andivelu I, Gandhesiri S. J. Org. Chem. 2014; 79: 4984 18e Li L.-T, Li H.-Y, Xing L.-J, Wen L.-J, Wang P, Wang B. Org. Biomol. Chem. 2012; 10: 9519 18f Zhang N, Cheng R, Zhang-Negrerie D, Du Y, Zhao K. J. Org. Chem. 2014; 79: 10581 18g Liu L, Du L, Zhang-Negrerie D, Du Y. RSC Adv. 2015; 5: 29774 18h Deb ML, Pegu CD, Borpatra PJ, Baruah PK. Tetrahedron Lett. 2016; 57: 5479 18i Chen W, Seidel D. Org. Lett. 2016; 18: 1024 18j Schweitzer-Chaput B, Klussmann M. Eur. J. Org. Chem. 2013; 666 18k Deb ML, Das C, Deka B, Saikia PJ, Baruah PK. Synlett 2016; 27: 2788 18l Pinter A, Sud A, Sureshkumar D, Klussmann M. Angew. Chem. Int. Ed. 2010; 49: 5004 18m Deb ML, Borpatra PJ, Saikia PJ, Baruah PK. Synlett 2017; 28: 461 18n Deb ML, Borpatra PJ, Pegu CD, Thakuria R, Saikia PJ, Baruah PK. ChemistrySelect 2017; 2: 140 18o Deb ML, Pegu CD, Borpatra PJ, Saikia PJ, Baruah PK. Green Chem. 2017; 19: 4036 18p Deb ML, Borpatra PJ, Baruah PK. Green Chem. 2019; 21: 69 19 Stavber S, Jereb M, Zupan M. Chem. Commun. 2002; 488 20 Kornblum N, Powers JW, Anderson GJ, Jones WJ, Larson HO, Levand O, Weaver WM. J. Am. Chem. Soc. 1957; 79: 6562 21a Bettanin L, Saba S, Galetto FZ, Mike GA, Rafique J, Braga AL. Tetrahedron Lett. 2017; 58: 4713 21b Siddaraju Y, Prabhu KR. Org. Biomol. Chem. 2017; 15: 5191 22 Ge W, Wei Y. Green Chem. 2012; 14: 2066 Zusatzmaterial Zusatzmaterial Supporting Information
