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

Zheng Lu; Yue Xu; Ze Wen; Changhong Xie; Chengyue Xie; Mengqian Yu; Lingyun Gao; Yong-Qing Yang; Ximing Xu

doi:10.1055/a-1931-6711

Synthesis, Table of Contents

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

Zheng Lu

,

Yue Xu

,

Ze Wen

,

Changhong Xie

,

Chengyue Xie

,

Mengqian Yu

,

Lingyun Gao

,

Yong-Qing Yang ∗

,

Ximing Xu∗

Abstract

All articles of this category

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

Key words

protective group - QPA - visible-light - photocatalyst - organo-reductant - Hantszch ester

Full Text

References

References

1a Bottecchia C, Noel T. Chem. Eur. J. 2019; 25: 26
1b Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
1c Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
1d Schultz DM, Yoon TP. Science 2014; 343: 1239176

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

17a Yang Y.-Q, Lu Z. Chin. J. Chem. 2014; 32: 650
17b Yang Y.-Q, Lu Z. Synthesis 2019; 51: 508

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

Supplementary Material

Supporting Information