One-Pot Synthesis of Bio-based Styrenes from β-(Phenyl)-β-(phenyl­thio)propionic Acids via Neutral Ionic Liquid, Microwave Irradiation Triggered Cascade Decarboxylative Dehydrosulfenylation

Richa Singh; Sumit K. Rastogi; Santosh Kumar; Danish Equbal; Yogesh Thopate; Arun K. Sinha

doi:10.1055/a-2528-5236

Synthesis, Table of Contents

Synthesis
DOI: 10.1055/a-2528-5236

paper

One-Pot Synthesis of Bio-based Styrenes from β-(Phenyl)-β-(phenylthio)propionic Acids via Neutral Ionic Liquid, Microwave Irradiation Triggered Cascade Decarboxylative Dehydrosulfenylation

Richa Singh

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

^bDepartment of Chemistry, Gaya College, Gaya, Bihar 23001, India

,

Sumit K. Rastogi

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

^cAcademy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India

,

Santosh Kumar

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

^cAcademy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India

,

Danish Equbal

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

,

Yogesh Thopate

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

^cAcademy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India

,

Arun K. Sinha∗

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow U.P.-226031, India

^cAcademy of Scientific and Innovative Research, Ghaziabad, U.P.-110001, India

› Author Affiliations

Abstract

All articles of this category

Abstract

A direct, new and eco-friendly strategy for the one-step synthesis of methoxylated and hydroxylated styrenes from β-(phenyl)-β-(phenylthio)propionic acids is reported. This approach utilizes a neutral ionic liquid [hmim]Br-triggered cascade decarboxylative dehydrosulfenylation reaction under microwave irradiation, without the need for strong bases, acids and toxic metal oxidants, and eliminates the need for a phenolic group protection–deprotection strategy, thus offering an efficient route to bio-based commercially important FEMA GRAS approved vinylphenols. NMR studies suggest a concerted reaction mechanism.

Key words

ionic liquids - microwave irradiation - deprotected - decarboxylative dehydrosulfenylation - styrenes

Full Text

References

References
1 Current address: A. K. Sinha, Sustainable Materials Research Centre (SUSMAT-RC), University Mohammed VI Polytechnic (UM6P), BenGuerir 43150, Morocco.

2a Chatonnet P, Dubourdieu D, Boidron J.-N, Lavigne V. J. Sci. Food Agric. 1993; 62: 191
2b Wen F, Zhang L, Wang P, Li L, Chen J, Chen C, Wu W, Wang G, Zhang S. J. Mater. Chem. A 2020; 8: 15122
2c Du H, Liu L, Zhang F, Leng J, Liu Y. Composites, Part B 2019; 173: 106905
2d Peterson AM. Addit. Manuf. 2019; 27: 363
2e Li Y, Zhang X, Lan J, Li D, Wang Z, Xu P, Sun J. ACS Sustainable Chem. Eng. 2021; 9: 2795
2f Dharmasivam M, Kaya B, Wijesinghe T, Azad MG, Gonzálvez MA, Hussaini M, Chekmarev J, Bernhardt PV, Richardson DR. J. Med. Chem. 2023; 66: 1426
2g Shard A, Sharma N, Bharti R, Dadhwal S, Kumar R, Sinha AK. Angew. Chem. Int. Ed. 2012; 51: 12250
2h Kumar R, Saima, Shard A, Andhare NH, Richa, Sinha AK. Angew. Chem. Int. Ed. 2015; 54: 828
2i Kumar R, Shard A, Bharti R, Thopate Y, Sinha AK. Angew. Chem. Int. Ed. 2012; 51: 2636
2j Sharma N, Mohanakrishnan D, Shard A, Sharma A, Saima, Sinha AK, Sahal D. J. Med. Chem. 2012; 55: 297
2k Shard A, Rawat K, Sinha AK, Padwal Y, Kumar D. Eur. J. Org. Chem. 2016; 5941
2l Xiong H, Li Y, Qian B, Wei R, Van der Eycken EV, Bao H. Org. Lett. 2019; 21: 776
2m Meng Q.-Y, Wang S, Huff G, König B. J. Am. Chem. Soc. 2018; 140: 3198
2n Basu B, Das S, Das P, Mandal B, Banerjee D, Almqvist F. Synthesis 2009; 1137
2o Masuda Y, Ikeshita D, Murakami M. Helv. Chim. Acta 2021; 104: e2000228
2p Wu S, Chen Y, Xu Y, Li A, Xu Q, Glieder A, Li Z. ACS Catal. 2014; 4: 409
2q Zhang J, Yang X, Dong R, Gao L, Li J, Li X, Huang S, Zhang C, Chang H. ACS Sustainable Chem. Eng. 2020; 8: 18277
2r Xiong Y, Sun W, Xin P, Chen W, Zheng X, Yan W, Zheng L, Dong J, Zhang J, Wang D, Li Y. Adv. Mater. 2020; 32: 2000896
2s Zhang Y, Iqbal A, Zai J, Zhang S.-Y, Guo H, Liu X, ul Islam I, Fazal H, Qian X. Org. Chem. Front. 2022; 9: 436
2t Rohde LN, Diver ST. Tetrahedron Lett. 2022; 108: 154121
2u Jagtap S. Catalysts 2017; 7: 267

3a Socolsky C, Salvatore A, Asakawa Y, Bardón A. ARKIVOC 2003; (x): 347
3b Janes D, Kantar D, Kreft S, Prosen H. Food Chem. 2008; 112: 120
3c Galano A, Márquez MF, Alvarez IJ. R. J. Phys. Chem. B 2011; 115: 8590
3d Zhang S, Mueller C. J. Agric. Food Chem. 2012; 60: 10433

4a Aslam SN, Stevenson PC, Phythian SJ, Veitch NC, Hall DR. Tetrahedron 2006; 62: 4214
4b Kalanoor BS, Bisht PB, Annamalai S, Aidhen IS. J. Lumin. 2009; 129: 1094
4c Wei Y, Chen C.-T. J. Am. Chem. Soc. 2007; 129: 7478
4d Zhao P, Chen J, Ma N, Chen J, Qin X, Liu C, Yao F, Yao L, Jin L, Cong Z. Chem. Sci. 2021; 12: 6307
4e Adamik R, Földesi T, Novák Z. Org. Lett. 2020; 22: 8091
4f Okita T, Asahara KK, Muto K, Yamaguchi J. Org. Lett. 2020; 22: 3205

5a Vaughan BA, Webster-Gardiner MS, Cundari TR, Gunnoe TB. Science 2015; 348: 421
5b Shekhah O, Ranke W, Schüle A, Kolios G, Schlögl R. Angew. Chem. Int. Ed. 2003; 42: 5760
5c Keller N, Maksimova NI, Roddatis VV, Schur M, Mestl G, Butenko YV, Schlögl R. Angew. Chem. Int. Ed. 2002; 41: 1885
5d Shekhah O, Ranke W, Schlögl R. J. Catal. 2004; 225: 56
5e Xu J, Xue B, Liu Y.-M, Li Y.-X, Cao Y, Fan K.-N. Appl. Catal., A 2011; 405: 142
5f Han Q, Li P, Yuan Y, Zhang X, Guo H, Xu L. Appl. Catal., A 2020; 605: 117807
5g Hong Z, Xiong C, Zhaoa G, Zhu Z. Catal. Sci. Technol. 2019; 9: 6828

6a Julia M, Paris J.-M. Tetrahedron Lett. 1973; 4833
6b Lee GH, Lee HK, Choi EB, Kim BT, Pak CS. Tetrahedron Lett. 1995; 36: 5607
6c Abramovitch A, Varghese JP, Marek I. Org. Lett. 2004; 6: 621
6d Baker-Glenn CA. G, Barrett AG. M, Gray AA, Procopioua PA, Ruston M. Tetrahedron Lett. 2005; 46: 7427
6e Wu J.-C, Gong L.-B, Xia Y, Song R.-J, Xie Y.-X, Li J.-H. Angew. Chem. Int. Ed. 2012; 51: 9909
6f Yao C.-Z, Li Q.-Q, Wang M.-M, Ning X.-S, Kang Y.-B. Chem. Commun. 2015; 51: 7729

7a Walling C, Wolfstrin KB. J. Am. Chem. Soc. 1947; 69: 852
7b Nomura E, Hosoda A, Mori H, Taniguchi H. Green Chem. 2005; 7: 863
7c Bernini R, Mincione E, Barontini M, Provenzano G, Setti L. Tetrahedron 2007; 63: 9663
7d Gooßen LJ, Linder C, Rodríguez N, Lange PP, Fromm A. Chem. Commun. 2009; 7173
7e Murray RE, Walter EL, Doll KM. ACS Catal. 2014; 4: 3517
7f Cahiez G, Moyeux A, Gager O, Poizat M. Adv. Synth. Catal. 2013; 355: 790
7g Dupuy S, Steven PN. Chem. Eur. J. 2013; 19: 14034
7h Cadot S, Rameau N, Mangematin S, Pinel C, Djakovitch L. Green Chem. 2014; 16: 3089

8 Stanton MP, Hoover JM. J. Org. Chem. 2023; 88: 1713

9a Liang L, Liu R, Foster KE. O, Choudhury A, Cook S, Cameron JC, Srubar WV, Gill RT. Metab. Eng. 2020; 57: 74
9b Grubbe WS, Rasor BJ, Krüger A, Jewett MC, Karim AS. Metab. Eng. 2020; 61: 89
9c Takemoto M, Achiwa K. Tetrahedron Lett. 1999; 40: 6595
9d Bassat AB, Breinig S, Crum GA, Huang L, Altenbaugh AL. B, Rizzo NR, Trotman J, Vannelli T, Sariaslani FS, Haynie SL. Org. Process Res. Dev. 2007; 11: 278
9e Fujiwara R, Noda S, Tanaka T, Kondo A. J. Biosci. Bioeng. 2016; 122: 730
9f Sharma UK, Sharma N, Salwan R, Kumar R, Kasana R, Sinha AK. J. Sci. Food Agric. 2012; 92: 610
9g Takemoto M, Achiwa K. Chem. Pharm. Bull. 2001; 49: 639
9h Sinha AK, Joshi BP, Sharma A. US Patent 2004/0118673 A1, 2004

10a Guimarães M, Mateus N, de Freitas V, Branco LC, Cruz L. J. Agric. Food Chem. 2020; 68: 7387
10b Leadbeater NE, Torenius HM. J. Org. Chem. 2002; 67: 3145
10c Wahidin S, Idris A, Shaleh SR. M. Bioresour. Technol. 2016; 206: 150
10d Bhatt JD, Patel TS, Chudasama CJ, Patel KD. ChemistrySelect 2018; 3: 3632
10e Andrade VP, Mittersteiner M, Lobo MM, Frizzo CP, Bonacorso HG, Martins MA, Zanatta N. Tetrahedron Lett. 2018; 59: 891

11 Kumar R, Sharma A, Sharma N, Kumar V, Sinha AK. Eur. J. Org. Chem. 2008; 5577

12a Chakraborti AK, Roy SR, Kumar D, Chopra P. Green Chem. 2008; 10: 1111
12b Thopate Y, Singh R, Sharma T, Siddiqi MI, Sinha AK. Asian J. Org. Chem. 2017; 6: 1867
12c Chakraborti AK, Roy SR. J. Am. Chem. Soc. 2009; 131: 6902
12d Roy SR, Chakraborti AK. Org. Lett. 2010; 12: 3866
12e Sarkar A, Roy SR, Chakraborti AK. Chem. Commun. 2011; 47: 4538

13a Sinha AK, Sharma A, Joshi BP. Tetrahedron 2007; 63: 960
13b Sharma A, Kumar R, Sharma N, Kumar V, Sinha AK. Adv. Synth. Catal. 2008; 350: 2910
13c Roy SR, Jadhavar PS, Seth K, Sharma KK, Chakraborti AK. Synthesis 2011; 2261
13d Sarkar A, Roy SR, Parikh N, Chakraborti AK. J. Org. Chem. 2011; 76: 7132

14 Cao X, Tsukamoto T, Seki T, Tanaka H, Morimura S, Cao L, Mizoshita T, Ban H, Toyoda T, Maeda H, Tatematsu M. Int. J. Cancer 2008; 122: 1445

15a Saima, Soni I, Lavekar AG, Shukla M, Equbal D, Sinha AK, Chopra S. Drug Dev. Res. 2019; 80: 171
15b Saima, Lavekar AG, Kumar R, Sinha AK. J. Mol. Catal. B: Enzym. 2015; 116: 113
15c Kumar R, Sharma N, Sharma UK, Shard A, Sinha AK. Adv. Synth. Catal. 2012; 354: 2107

16a Law MC, Wong KY, Chan TH. Green Chem. 2002; 4: 328
16b Nockemann P, Binnemans K, Driesen K. Chem. Phys. Lett. 2005; 415: 131
16c Handy ST, Okello M. J. Org. Chem. 2005; 70: 1915

17 Gao S, Tzeng T, Sastry MN. V, Chu C.-M, Liu J.-T, Lin C, Yao C.-F. Tetrahedron Lett. 2006; 47: 1889

Supplementary Material

Supporting Information

One-Pot Synthesis of Bio-based Styrenes from β-(Phenyl)-β-(phenyl­thio)propionic Acids via Neutral Ionic Liquid, Microwave Irradiation Triggered Cascade Decarboxylative Dehydrosulfenylation

One-Pot Synthesis of Bio-based Styrenes from β-(Phenyl)-β-(phenylthio)propionic Acids via Neutral Ionic Liquid, Microwave Irradiation Triggered Cascade Decarboxylative Dehydrosulfenylation