Gram-Scale Synthesis of β-Sulfonyl Styrenes

Meng-Yang Chang; Yan-Shin Wu; Yu-Ting Hsiao

doi:10.1055/s-0037-1610822

Synthesis, Table of Contents

Synthesis 2018; 50(23): 4651-4658
DOI: 10.1055/s-0037-1610822

paper

Gram-Scale Synthesis of β-Sulfonyl Styrenes

Authors

Meng-Yang Chang*

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Email: mychang@kmu.edu.tw

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
Yan-Shin Wu

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Email: mychang@kmu.edu.tw
Yu-Ting Hsiao

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Email: mychang@kmu.edu.tw

Abstract

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Abstract

A simple and gram-scale synthesis of β-sulfonyl styrenes has been developed starting from one-pot PPA (polyphosphoric acid)-catalyzed 1,1-diacetoxylation of arylacetaldehydes (ArCH₂CHO) with acetic anhydride (Ac₂O) followed by deacetoxylative sulfonylation of the resulting 1,1-diacetate intermediate with sodium sulfinates (RSO₂Na) in good yields under solvent-free conditions.

Key words

β-sufonyl styrenes - sodium sulfinates - arylacetaldehydes - gram-scale synthesis

Full Text

References

References
1 For leading references, see: Fang Y. Luo Z. Xu X. RSC Adv. 2016; 6: 59661

2a Pandey G. Tiwari KN. Puranik VG. Org. Lett. 2008; 11: 3611
2b Zhu Q. Lu Y. Org. Lett. 2009; 11: 1721
2c Mauleon P. Carretero JC. Chem. Commun. 2005; 4961
2d Schneider TH. Rieger M. Ansorg K. Sobolev AN. Schirmeister T. Engels B. Grabowsky S. New J. Chem. 2015; 39: 5841

3a Wardrop DJ. Fritz J. Org. Lett. 2006; 8: 3659
3b Piccardi R. Renaud P. Eur. J. Org. Chem. 2007; 4752
3c McLaughlin NP. Evans P. J. Org. Chem. 2010; 75: 518
3d Zhao P. Beaudry CM. Angew. Chem. Int. Ed. 2014; 53: 10500

4a Bachovchin D. Zuhl A. Speers A. Wolfe M. Weerapana E. Brown S. Rosen H. Cravatt B. J. Med. Chem. 2011; 54: 5229
4b Santos MM. M. Moreira R. Mini-Rev. Med. Chem. 2007; 7: 1040
4c Palmer JT. Rasnick D. Klaus JL. Bromme D. J. Med. Chem. 1995; 38: 3193
4d Dunny E. Doherty W. Evans P. Malthouse JP. G. Nolan D. Knox AJ. S. J. Med. Chem. 2013; 56: 6638

5a Ortega-Munoz M. Morales-Sanfrutos J. Megia-Fernandez A. Lopez-Jaramillo FJ. Hernandez-Mateo F. Santoyo-Gonzalez F. J. Mater. Chem. 2010; 20: 7189
5b Wang H. Cheng F. Li M. Peng W. Qu J. Langmuir 2015; 31: 3413
5c Zhou J. Chen P. Deng C. Meng F. Cheng R. Zhong Z. Macromolecules 2013; 46: 6723

6 Xue Q. Mao Z. Shi Y. Mao H. Cheng Y. Zhu C. Tetrahedron Lett. 2012; 53: 1851
7 Sawangphon T. Katrun P. Chaisiwamongkhol K. Pohmakotr M. Reutrakul V. Jaipetch T. Soorukram D. Kuhakarn C. Synth. Commun. 2012; 43: 1692
8 Doherty W. Evans P. J. Org. Chem. 2016; 81: 1416
9 Qian H. Huang X. Synlett 2001; 1913

Sulfonylative coupling of DMSO and styrenes or acetylenes, for Cu(I), see:

10a Jiang Y. Loh T.-P. Chem. Sci. 2014; 5: 4939
10b Yuan G. Zheng J. Gao X. Li X. Huang L. Chen H. Jiang H. Chem. Commun. 2012; 48: 7513

For Cu(II), see:

10c Chen J.-Y. Chen X.-L. Li X. Qu L.-B. Zhang Q. Duan L.-K. Xia Y.-Y. Chen X. Sun K. Liu Z.-D. Zhao Y.-F. Eur. J. Org. Chem. 2015; 314

For NH₄I, see:

10d Gao X. Pan X. Gao J. Huang H. Yuan G. Li Y. Chem. Commun. 2015; 51: 210

Decarboxylative coupling of cinnamic acids and RSO₂Na, for Pd(II)/Ag(I), see:

11a Guo R. Gui Q. Wang D. Tan Z. Catal. Lett. 2014; 144: 1377

For Cu(II), see:

11b Jiang Q. Xu B. Jia J. Zhao A. Shao Y.-R. Li Y.-Y. He N.-N. Guo C.-C. J. Org. Chem. 2014; 79: 7372

For Mn(III), see:

11c Xue N. Guo R. Tu X. Luo W. Deng W. Synlett 2016; 27: 2695

For DIB, see:

11d Katrun P. Hlekhlai S. Meesin J. Pohmakotr M. Reutrakul V. Jaipetch T. Soorukram D. Kuhakarn C. Org. Biomol. Chem. 2015; 13: 4785

For I₂, see:

11e Gao J. Lai J. Yuan G. RSC Adv. 2015; 5: 66723

For K₂CO₃, see:

11f Xu Y. Tang X. Hu W. Wu W. Jiang H. Green Chem. 2014; 16: 3720

For electrolysis, see:

11g Qian P. Bi M. Su J. Zha Z. Wang Z. J. Org. Chem. 2016; 81: 4876

Nucleophilic substitution of arylacetylenes and RSO₂Na, for Cu(I), see:

12a Taniguchi N. Synlett 2012; 23: 1245
12b Taniguchi N. Tetrahedron 2014; 70: 1984

For Cu(II), see:

12c Shelke GM. Rao VK. Pericherla K. Kumar A. Synlett 2014; 25: 2345

For H₃PO₄, see:

12d Rong G. Mao J. Yan H. Zheng Y. Zhang G. J. Org. Chem. 2015; 80: 7652

For Pd(II), see:

12e Xu Y. Zhao J. Tang X. Wu W. Jiang H. Adv. Synth. Catal. 2014; 356: 2029

Nucleophilic substitution of styrenes and RSO₂Na, for Cu(I), see:

13a Taniguchi N. Synlett 2011; 1308

For KI/NaIO₄, see:

13b Das B. Lingaiah M. Damodar K. Bhunia N. Synthesis 2011; 2941

For NaI/CAN, see:

13c Nair V. Augustine A. Suja TD. Synthesis 2002; 2259

For expoxides, see:

14a Chawla R. Kapoor R. Singh AK. Yadav LD. S. Green Chem. 2012; 14: 1308

For vicinal dibromides, see:

14b Guan Z.-H. Zuo W. Zhao L.-B. Ren Z.-H. Liang Y.-M. Synthesis 2007; 1465

For vinyl bromides, see:

14c Liang S. Zhang R.-Y. Wang G. Chen S.-Y. Yu X.-Q. Eur. J. Org. Chem. 2013; 7050
14d Bian M. Xu F. Ma C. Synthesis 2007; 2951

For vinyl boronic acids, see:

14e Yang H. Li Y. Jiang M. Wang J. Fu H. Chem. Eur. J. 2011; 17: 5652
14f Huang F. Batey RA. Tetrahedron 2007; 63: 7667
14g Kar A. Sayyed IA. Lo WF. Kaiser HM. Beller M. Tse MK. Org. Lett. 2007; 9: 3405

For vinyl sulfides, see:

14h Lin Y.-m. Lu G.-p. Wang R.-k. Yi W.-b. Org. Lett. 2017; 19: 1100

Nucleophilic substitution of arylacetylenes and RSO₂Cl, for In(III), see:

15a Deng G. Zou J. ARKIVOC 2010; (ii): 186

For Ag(I), see:

15b Deng GS. Sun TF. Chin. Chem. Lett. 2012; 23: 1115

For Fe(II), see:

15c Zeng X. Ilies L. Nakamura E. Org. Lett. 2012; 14: 954

Cross-coupling of styrenes and RSO₂NHNH₂, for Cu(I), see:

16a Li X. Xu Y. Wu W. Jiang C. Qi C. Jiang H. Chem. Eur. J. 2014; 20: 7911

For I₂/TBHP, see:

16b Singh R. Allam BK. Singh N. Kumari K. Singh SK. Singh KN. Org. Lett. 2015; 17: 2656

For photolysis, see:

16c Cai S. Xu Y. Chen D. Li L. Chen Q. Huang M. Weng W. Org. Lett. 2016; 18: 2990

17a Kochhar KS. Bal BS. Deshpande RP. Rajadhyaksha SN. Pinnick HW. J. Org. Chem. 1983; 48: 1765
17b Reddy BM. Sreekanth PM. Khan A. Synth. Commun. 2004; 34: 1839
17c Kumar P. Hegda VR. Kumar TP. Tetrahedron Lett. 1995; 36: 601
17d Yadav JS. Reddy BV. S. Venugopal C. Ramalingam T. Synlett 2002; 604
17e Jin TS. Sun G. Li YW. Li TS. Green Chem. 2002; 4: 255
17f Ogiwara Y. Takahashi K. Kitazawa T. Sakai N. J. Org. Chem. 2015; 80: 3101 ; and references cited therein
17g Yadav JS. Subba Reddy BV. Kiran Kumar Reddy GS. Tetrahedron Lett. 2000; 41: 2695

18a Chang M.-Y. Lee T.-W. Wu M.-H. Org. Lett. 2012; 14: 2198
18b Chang M.-Y. Hsiao Y.-T. J. Org. Chem. 2017; 82: 11594
18c Chan C.-K. Tsai Y.-L. Chang M.-Y. Org. Lett. 2017; 19: 1358

For divinylsulfones, see:

19a Paradies J. Synthesis 2010; 947
19b Bieniek M. Koloda D. Grela K. Org. Lett. 2006; 8: 5689
19c Pal TK. Dey S. Pathak T. J. Org. Chem. 2011; 76: 3034 ; and references cited therein

For biological activities of styryl sulfones, see:

20a Reddy MV. R. Mallireddigari MR. Cosenza SC. Pallela VR. Iqbal NM. Robell KA. Kang AD. Reddy EP. J. Med. Chem. 2008; 51: 86
20b Reddy MV. R. Venkatapuram P. Mallireddigari MR. Pallela VR. Cosenza SC. Robell KA. Akula B. Hoffman BS. Reddy EP. J. Med. Chem. 2011; 54: 6254
20c Vedula MS. Pulipaka AB. Venna C. Chintakuta VK. Jinnapally S. Kattuboina VA. Vallakati V. Akella V. Rajgopal S. Reka AK. Teepireddy SK. Mammoor PK. Rajagopalan R. Bulusu G. Khandelwal A. Upreti VV. Mamidi SR. Eur. J. Med. Chem. 2003; 38: 811
20d Adler V. Franklin CC. Kraft AS. Proc. Natl. Acad. Sci. U.S.A. 1992; 89: 5341
20e Lu M. Merali S. Gordon R. Jiang J. Li Y. Mandeli J. Duan X. Fallon J. Holland JF. Genes Cancer 2011; 2: 985
20f Gumireddy K. Reddy MV. R. Cosenza SC. Nathan RB. Baker SJ. Papathi N. Jiang J. Holland J. Reddy EP. Cancer Lett. 2005; 7: 275
20g Reddy EP. Reddy MV. R. US Patent 6359013 B1, 2002

For reviews on synthesis of chromenes, see:

21a Majumdar N. Paul ND. Mandal S. de Bruin B. Wulff WD. ACS Catal. 2015; 5: 2329
21b Shi Y.-L. Shi M. Org. Biomol. Chem. 2007; 5: 1499
21c Ferreira SB. da Silva F. deC. Pinto AC. Gonzaga DT. G. Ferreira VF. J. Heterocycl. Chem. 2009; 46: 1080
21d Ellis GP. Lockhart IM. The Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones . Vol. 31. Ellis GP. Wiley-VCH; Weinheim: 2009: 1-1196

22a Rokade BV. Prabhu KR. J. Org. Chem. 2014; 79: 8110
22b Chen J. Mao J. Zheng Y. Liu D. Rong G. Yan H. Zhang C. Shi D. Tetrahedron 2015; 71: 5059
22c Liu XT. Ding ZC. Ju LC. Xu SX. Zhan ZP. Synthesis 2017; 49: 1575
22d Terentev AO. Mulina OM. Pirgach DA. Ilovaisky AI. Syroeshkin MA. Kapustina NI. Nikishin GI. Tetrahedron 2017; 73: 6871
22e Kadari L. Palakodety RK. Yallapragada LP. Org. Lett. 2017; 19: 2580
22f Zhao Y. Lai YL. Du KS. Lin DZ. Huang JM. J. Org. Chem. 2017; 82: 9655

Supplementary Material

Supporting Information (PDF)