Synthesis 2022; 54(22): 5026-5034
DOI: 10.1055/a-1846-5598
special topic
Aryne Chemistry in Synthesis

Poly(ethylene glycol) Dimethyl Ethers (PEGDME): Efficient and Recyclable Solvents for Aryne-Involved Reactions

Shweta Rai
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
Polasani Samatha
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
,
Ramunaidu Addipilli
b   Centre for Mass Spectrometry, Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
Prabhakar Sripadi
b   Centre for Mass Spectrometry, Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
› Institutsangaben


Abstract

A variety of aryne reactions are demonstrated in poly(ethylene glycol) dimethyl ethers (PEGDMEs) as solvents without the need of any additive. The reactions proceed efficiently and good yields of the desired products are observed with PEGDME. Further, the advantage of being able to recycle PEG solvents is demonstrated in this work.

Supporting Information



Publikationsverlauf

Eingereicht: 23. März 2022

Angenommen nach Revision: 09. Mai 2022

Accepted Manuscript online:
09. Mai 2022

Artikel online veröffentlicht:
20. Juni 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Stoermer R, Kahlert B. Ber. Dtsch. Chem. Ges. 1902; 35: 1633
    • 2a Matsumoto T, Hosoya T, Katsuki M, Suzuki K. Tetrahedron Lett. 1991; 32: 6735
    • 2b Olofson RA, Dougherty CM. J. Am. Chem. Soc. 1973; 95: 582
    • 2c Campbell CD, Rees CW. Proc. Chem. Soc. 1964; 296
    • 2d Stiles M, Miller RG. J. Am. Chem. Soc. 1960; 82: 3802
    • 2e Heaney H, Mann FG, Millar IT. J. Chem. Soc. 1957; 3930
    • 3a Shi J, Li L, Li Y. Chem. Rev. 2021; 121: 3892
    • 3b Roy T, Biju AT. Chem. Commun. 2018; 54: 2580
    • 3c Asamdi M, Chikhalia KH. Asian J. Org. Chem. 2017; 6: 1331
    • 3d Bhojgude SS, Bhunia A, Biju AT. Acc. Chem. Res. 2016; 49: 1658
    • 3e Goetz AE, Shah TK, Garg NK. Chem. Commun. 2015; 51: 34
    • 3f Bhojgude SS, Biju AT. Angew. Chem. 2012; 124: 1550
    • 3g Dubrovskiy AV, Markina NA, Larock RC. Org. Biomol. Chem. 2013; 11: 191
    • 3h Bhunia A, Yetra SR, Biju AT. Chem. Soc. Rev. 2012; 41: 3140
    • 3i Tadross PM, Stoltz BM. Chem. Rev. 2012; 112: 3550
    • 3j Sanz R. Org. Prep. Proced. Int. 2008; 40: 215
    • 3k Pellissier H, Santelli M. Tetrahedron 2003; 59: 701
    • 3l Wenk HH, Winkler M, Sander W. Angew. Chem. Int. Ed. 2003; 42: 502
    • 3m Himeshima Y, Sonoda T, Kobayashi H. Chem. Lett. 1983; 12: 1211
    • 4a Buschmann H.-J, Mutihac R.-C, Schollmeyer E. Thermochim. Acta 2008; 472: 17
    • 4b Kikuchi Y, Sakamoto Y. Anal. Chim. Acta 2000; 403: 325
    • 4c Wynn DA, Roth MM, Pollard BD. Talanta 1984; 31: 1036
    • 4d Liotta CL, Harris HP. J. Am. Chem. Soc. 1974; 96: 2250
    • 5a Li M, Song W, Dong K, Zheng Y. Tetrahedron Lett. 2020; 61: 151503
    • 5b Steed JW. Coord. Chem. Rev. 2001; 215: 171
    • 6a Vafaeezadeh M, Hashemi MM. J. Mol. Liq. 2015; 207: 73
    • 6b Colacino E, Martinez J, Lamaty F, Patrikeeva LS, Khemchyan LL, Ananikov VP, Beletskaya IP. Coord. Chem. Rev. 2012; 256: 2893
    • 6c Chandrasekhar S, Prakash SJ, Rao CL. J. Org. Chem. 2006; 71: 2196
    • 6d Chandrasekhar S, Narsihmulu Ch, Sultana SS, Reddy NR. Org. Lett. 2002; 4: 4399
    • 7a Soni J, Sahiba N, Sethiya A, Agarwal S. J. Mol. Liq. 2020; 315: 113766
    • 7b Chen J, Spear SK, Huddleston JG, Rogers RD. Green. Chem. 2005; 7: 64
    • 7c Poly(ethylene glycol): Chemistry and Biological Applications . Harris JM, Zalipsky S. ACS Symposium Series 680; American Chemical Society; Washington DC: 1997
    • 8a Yu T, Guo M, Wen S, Zhao R, Wang J, Sun Y, Liu Q, Zhou H. RSC Adv. 2021; 11: 13848
    • 8b Liu K.-J, Deng J.-H, Yang J, Gong S.-F, Lin Y.-W, He J.-Y, Cao Z, He W.-M. Green Chem. 2020; 22: 433
    • 8c Steinbauer J, Werner T. ChemSusChem 2017; 10: 3025
    • 8d Ha SJ, Jung E.-Y, Kim WM, Lee JC. Bull. Korean Chem. Soc. 2014; 35: 629
    • 8e Xu L, Lam KH, Ji J, Wu J, Fan Q.-H, Lo W.-H, Chan AS. C. Chem. Commun. 2005; 1390
  • 9 Yoshida S, Hazama Y, Sumida Y, Yano T, Hosoya T. Molecules 2015; 20: 10131
    • 10a Sanjeev K, Raju S, Chandrasekhar S. Org. Lett. 2021; 23: 4013
    • 10b Venkatesh T, Mainkar PS, Chandrasekhar S. Org. Biomol. Chem. 2019; 17: 2192
    • 10c Kallepu S, Sanjeev K, Chegondi R, Mainkar PS, Chandrasekhar S. Org. Lett. 2018; 20: 7121
    • 10d Gouthami P, Chavan LN, Chegondi R, Chandrasekhar S. J. Org. Chem. 2018; 83: 3325
    • 10e Gouthami P, Chegondi R, Chandrasekhar S. Org. Lett. 2016; 18: 2044
    • 10f Kranthikumar R, Chegondi R, Chandrasekhar S. J. Org. Chem. 2016; 81: 2451
  • 11 Adepu R, Dhanaji JR, Samatha P, Mainkar PS, Chandrasekhar S. Org. Lett. 2020; 22: 8224
  • 12 Zhao M.-N, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Chem. Commun. 2012; 48: 8105
  • 13 Guin A, Gaykar RN, Bhattacharjee S, Biju AT. J. Org. Chem. 2019; 84: 12692
  • 14 Yoshida H, Watanabe M, Ohshita J, Kunai A. Chem. Commun. 2005; 3292
  • 15 Holden CM, Sohel SM. A, Greaney MF. Angew. Chem. Int. Ed. 2016; 55: 2450
  • 16 Bhattacharjee S, Guin A, Gaykar RN, Biju AT. Org. Lett. 2019; 21: 4383
  • 17 Gaykar RN, Guin A, Bhattacharjee S, Biju AT. Org. Lett. 2019; 21: 9613
  • 18 Li S.-J, Han L, Tian S.-K. Chem. Commun. 2019; 55: 11255
  • 19 Bhattacharjee S, Deswal S, Manoj N, Jindal G, Biju AT. Org. Lett. 2021; 23: 9083
  • 20 Bhattacharjee S, Guin A, Gaykar RN, Biju AT. Org. Lett. 2020; 22: 9097
  • 21 Zhou Y, Chi Y, Zhao F, Zhang W.-X, Xi Z. Chem. Eur. J. 2014; 20: 2463
  • 22 Bhunia A, Kaicharla T, Porwal D, Gonnadeb RG, Biju AT. Chem. Commun. 2014; 50: 11389
  • 23 Jeganmohan M, Bhuvaneswari S, Cheng C.-H. Chem. Asian J. 2010; 5: 153
  • 24 Kumar S, Jain SL. Ind. Eng. Chem. Res. 2014; 53: 541