Synthesis 2023; 55(03): 473-480
DOI: 10.1055/a-1931-6711
paper

A Visible-Light-Driven Approach to Free Alcohol from Esters of Quinone Propionic Acid

,
Yue Xu
,
Ze Wen
,
Changhong Xie
,
Chengyue Xie
,
Mengqian Yu
,
Lingyun Gao
,
,
Ximing Xu
Jiangsu University (No. 10JDG042 & No. 14JDG018) and National Key R & D Program of China (2018YFE0208600).


This paper is dedicated to Prof. Xiyan Lu on the occasion of his 94th birthday.

Abstract

Release of alcohol from quinone propionic esters (QPEs) propelled by visible-light is reported. 1°, 2°, and allylic alcohols could be freed from the corresponding QPEs under radiation from blue LED bulb in the presence of a photocatalyst. Ten examples are listed and the yields are good to excellent. Possible mechanism has been proposed and further applications of quinone propionic acid (QPA) in photochemistry would be expected.

Supporting Information



Publikationsverlauf

Eingereicht: 31. Juli 2022

Angenommen nach Revision: 26. August 2022

Accepted Manuscript online:
26. August 2022

Artikel online veröffentlicht:
10. Oktober 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 2a Weinstain R, Slanina T, Kand D, Klán P. Chem. Rev. 2020; 120: 13135
    • 2b Yang YQ, Lu Z, Xu X. Asian J. Org. Chem. 2019; 8: 2192
    • 2c Josa-Culleré L, Llebaria A. ChemPhotoChem 2021; 5: 296
    • 2d Thum MD, Falvey DE. J. Phys. Chem. A 2018; 122: 3204
    • 2e Paul A, Biswas A, Sinha S, Shah SS, Bera M, Mandal M, Singh ND. P. Org. Lett. 2019; 21: 2968
    • 3a Milstien S, Cohen LA. Proc. Natl. Acad. Sci. U.S.A. 1970; 67: 1143
    • 3b Thanassi JW, Cohen LA. Biochim. Biophys. Acta 1969; 172: 389
    • 4a Borchardt RT, Cohen LA. J. Am. Chem. Soc. 1972; 94: 9175
    • 4b Milstien S, Cohen LA. J. Am. Chem. Soc. 1972; 94: 9158
    • 4c Borchardt RT, Cohen LA. J. Am. Chem. Soc. 1973; 95: 8319
  • 5 Winans RE, Wilcox CF. J. Am. Chem. Soc. 1976; 98: 4281
  • 6 Carpino LA, Triolo SA, Berglund RA. J. Org. Chem. 1989; 54: 3303
  • 7 Cadenas E. Biochem. Pharmacol. 1995; 49: 127
  • 8 Sung Y.-M, Gayam SR, Hsieh P.-Y, Hsu H.-Y, Diau EW.-G, Wu S.-P. ACS Appl. Mater. Interfaces 2015; 7: 25961
    • 9a Ma D, Wang H, Ugo T, Mustafa D, Zhou W, Cali JJ. Photochem. Photobiol. 2021; 97: 1407
    • 9b Levine MN, Raines RT. Chem. Sci. 2012; 3: 2412
    • 9c Dai M, Song CW, Yang YJ, Kim HR, Reo YJ, Ahn KH. Sens. Actuators, B 2021; 330: 129277
    • 10a Gayam SR, Venkatesan P, Sung Y.-M, Sung S.-Y, Hu S.-H, Hsu H.-Y, Wu S.-P. Nanoscale 2016; 8: 12307
    • 10b Cho H, Bae J, Garripelli VK, Anderson JM, Jun H.-W, Jo S. Chem. Commun. 2012; 48: 6043
    • 10c Volpato M, Abou-Zeid N, Tanner RW, Glassbrook LT, Taylor J, Stratford I, Loadman PM, Jaffar M, Phillips RM. Mol. Cancer Ther. 2007; 6: 3122
    • 10d Ong W, Yang Y, Cruciano AC, McCarley RL. J. Am. Chem. Soc. 2008; 130: 14739
    • 10e Yan D, Xu X, Ren C, Chen C, Luo J, Han C, Kong L. Acta Biomater. 2021; 125: 267
    • 11a Suebsakwong P, Wang J, Khetkam P, Weerapreeyakul N, Wu J, Du Y, Yao Z.-J, Li J.-X, Suksamrarn A. ACS Med. Chem. Lett. 2019; 10: 1400
    • 11b Fang L, Qin X, Zhao J, Gou S. Inorg. Chem. 2019; 58: 2191
    • 11c Zhang X, Li X, Li Z, Wu X, Wu Y, You Q, Zhang X. Org. Lett. 2018; 20: 3635
    • 11d Chen Z, Li B, Xie X, Zeng F, Wu S. J. Mater. Chem. B 2018; 6: 2547
    • 11e Shin WS, Han J, Verwilst P, Kumar R, Kim J.-H, Kim JS. Bioconjugate Chem. 2016; 27: 1419
    • 11f Pitchuanchom S, Songsiang U, Weerapreeyakul N, Yenjai C. Lett. Drug Des. Discovery 2011; 8: 536
    • 11g Weerapreeyakul N, Anorach R, Khuansawad T, Yenjai C, Isaka M. Chem. Pharm. Bull. 2007; 55: 930
    • 12a Yang Q, Wen Y, Xu J, Shao S. Talanta 2020; 216: 120982
    • 12b Zhu Y, Han J, Zhang Q, Zhao Z, Wang J, Xu X, Hao H, Zhang J. RSC Adv. 2019; 9: 26729
    • 12c Yuan Z, Xu M, Wu T, Zhang X, Shen Y, Ernest U, Gui L, Wang F, He Q, Chen H. Talanta 2019; 198: 323
    • 12d Punganuru SR, Madala HR, Arutla V, Zhang R, Srivenugopal KS. Sci. Rep. 2019; 9: 1
    • 12e Cheng Z, Valenca WO, Dias GG, Scott J, Barth ND, de Moliner F, Souza GB. P, Mellanby RJ, Vendrell M, da Silva Junior EN. Bioorg. Med. Chem. 2019; 27: 3938
    • 12f Best QA, Prasai B, Rouillere A, Johnson AE, McCarley RL. Chem. Commun. 2017; 53: 783
    • 12g Zhou W, Leippe D, Duellman S, Sobol M, Vidugiriene J, O’Brien M, Shultz JW, Kimball JJ, DiBernardo C, Moothart L, Bernad L, Cali J, Klaubert DH, Meisenheimer P. ChemBioChem 2014; 15: 670
  • 13 Carpino LA, Nowshad F. Tetrahedron Lett. 1993; 34: 7009
  • 14 Görner H. Photochem. Photobiol. 2003; 78: 440
  • 15 Regan CJ, Walton DP, Shafaat OS, Dougherty DA. J. Am. Chem. Soc. 2017; 139: 4729
    • 16a Larionova NA, Ondozabal JM, Cambeiro XC. Adv. Synth. Catal. 2021; 363: 558
    • 16b Chen X, Qiao Z, Hou B, Jiang H, Gong W, Dong J, Li H.-Y, Cui Y, Liu Y. Nano Res. 2021; 14: 466
    • 16c Zhu D.-L, Wu Q, Li H.-Y, Li H.-X, Lang J.-P. Chem. Eur. J. 2020; 26: 3484
    • 16d Zhang X, Fang W.-Y, Lekkala R, Tang W, Qin H.-L. Adv. Synth. Catal. 2020; 362: 3358
    • 16e Wang J, Shao Z, Tan K, Tang R, Zhou Q, Xu M, Li Y.-M, Shen Y. J. Org. Chem. 2020; 85: 9944
    • 16f Wakchaure VN, Obradors C, List B. Synlett 2020; 31: 1707
    • 16g Shen G.-B, Fu Y.-H, Zhu X.-Q. J. Org. Chem. 2020; 85: 12535
    • 16h Scharinger F, Palvoelgyi AM, Zeindlhofer V, Schnuerch M, Schroeder C, Bica-Schroeder K. ChemCatChem 2020; 12: 3776
    • 16i Nagode SB, Kant R, Rastogi N. Chem. Asian J. 2020; 15: 3513
    • 16j Lin S, Chen Y, Li F, Shi C, Shi L. Chem. Sci. 2020; 11: 839
    • 16k Li Y.-L, Li W.-D, Gu Z.-Y, Chen J, Xia J.-B. ACS Catal. 2020; 10: 1528
    • 16l Li F.-s, Chen Y.-q, Lin S.-j, Shi C.-z, Li X.-y, Sun Y.-c, Guo Z.-w, Shi L. Org. Chem. Front. 2020; 7: 3434
    • 16m Leitch JA, Rogova T, Duarte F, Dixon DJ. Angew. Chem. Int. Ed. 2020; 59: 4121
    • 16n Konev MO, Cardinale L, Jacobi von Wangelin A. Org. Lett. 2020; 22: 1316
    • 16o Gualandi A, Calogero F, Mazzarini M, Guazzi S, Fermi A, Bergamini G, Cozzi PG. ACS Catal. 2020; 10: 3857
    • 16p Ding H, Sakata K, Kuriyama S, Nishibayashi Y. Organometallics 2020; 39: 2130
    • 16q Zheng C, Wang G.-Z, Shang R. Adv. Synth. Catal. 2019; 361: 4500
    • 16r Wu J, Grant PS, Li X, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2019; 58: 5697
    • 16s Wang P.-Z, Chen J.-R, Xiao W.-J. Org. Biomol. Chem. 2019; 17: 6936
  • 18 Cano R, Yus M, Ramón DJ. Tetrahedron 2011; 67: 8079
  • 19 Cárdenas J, Morales-Serna J, García-Ríos E, Bernal J, Paleo E, Gaviño R. Synthesis 2011; 1375
  • 20 Dieskau AP, Begouin JM, Plietker B. Eur. J. Org. Chem. 2011; 5291
  • 21 Prabhu K, Maddani M. Synlett 2011; 821
  • 22 Palumbo G, Pedatella S, Guaragna A, D’Alonzo D, De Nisco M. Synthesis 2006; 305
  • 23 Dieskau AP, Plietker B. Org. Lett. 2011; 13: 5544
  • 24 Yang J, Dai L, Wang X, Chen Y. Tetrahedron 2011; 67: 1456
  • 25 Negishi S, Ishibashi H, Matsuo J.-i. Org. Lett. 2010; 12: 4984