Recent Advances in Photoacid Catalysis for Organic Synthesis

Abstract

Photoacids are molecules that become more acidic upon the absorption of light. This short review highlights recent advances in the use of photoacids as catalysts for organic synthesis. Photoacid-catalyzed­ transformations discussed herein include: Protonation, glycosylation, acetalization, and arylation reactions.

1 Introduction

2 Protonation: Excited-State Proton Transfer (ESPT)

3 Glycosylation

4 Acetalization

5 Friedel–Crafts Arylation

6 Additional C–C and C–S Bond-Forming Reactions

7 Conclusion

Key words

photoacid catalysis - photochemistry - light-activation - in situ acid generation - excited-state proton transfer (ESPT) catalysis

Publication History

Received: 01 August 2020

Accepted after revision: 25 August 2020

Article published online:
19 October 2020

• References


Reviews on photocatalysis:
• 1a Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
• 1b Nicewicz DA, Nguyen TM. ACS Catal. 2014; 4: 355
• 1c Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
• 1d Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
• 2a Shirai M, Tsunooka M. Prog. Polym. Sci. 1996; 21: 1
• 2b Fu C, Xu J, Boyer C. Chem. Commun. 2016; 52: 7126
• 2c Patel PK, Arias JE, Gongora RS, Hernandez FE, Moncomble A, Aloise S, Chumbimuni-Torres KY. Phys. Chem. Chem. Phys. 2018; 20: 26804
• 2d Kagel H, Frohme M, Glökler J. J. Cell. Biotechnol. 2018; 4: 23
• 3 Förster T. Naturwissenschaften 1949; 36: 186
• 4 Weller A. Naturwissenschaften 1955; 42: 175

Reviews on photoacids:
• 5a Ireland JF, Wyatt PA. H. Adv. Phys. Org. Chem. 1976; 12: 131
• 5b Arnaut LG, Formosinho SJ. J. Photochem. Photobiol., A 1993; 75: 1
• 5c Shizuka H. Acc. Chem. Res. 1985; 18: 141
• 5d Tolbert LM, Solntsev KM. Acc. Chem. Res. 2002; 35: 19
• 5e Liao Y. Acc. Chem. Res. 2017; 50: 1956
• 5f Martin CJ, Rapenne G, Nakashima T, Kawai T. J. Photochem. Photobiol., C 2018; 34: 41
• 5g Zivic N, Kuroishi PK, Dumur F, Gigmes D, Dove AP, Sardon H. Angew. Chem. Int. Ed. 2019; 58: 10410
• 5h Kuznetsova NA, Malkov GV, Gribov BG. Russ. Chem. Rev. 2020; 89: 173
• 6 Tolbert LM, Haubrich JE. J. Am. Chem. Soc. 1994; 116: 10593
• 7 Weller AZ. Z. Elektrochem. 1960; 64: 55

Computational studies on photoacidity:
• 8a Acharya A, Chaudhuri S, Batista VS. J. Chem. Theory Comput. 2018; 14: 867
• 8b Wang Y.-F, Cheng Y.-C. Phys. Chem. Chem. Phys. 2018; 20: 4351

Reviews on catalytic protonation strategies:
• 9a Mohr JT, Hong AY, Stoltz BM. Nat. Chem. 2009; 1: 359
• 9b Oudeyer S, Brière J.-F, Levacher V. Eur. J. Org. Chem. 2014; 6103
• 10 Das A, Banerjee T, Hanson K. Chem. Commun. 2016; 52: 1350
• 11a McClure DS. J. Chem. Phys. 1949; 17: 665
• 11b McClure DS, Blake NW, Hanst PL. J. Chem. Phys. 1954; 22: 255
• 12a Das A, Ayad S, Hanson K. Org. Lett. 2016; 18: 5416
• 12b Posey V, Hanson K. ChemPhotoChem 2019; 3: 580
• 13 Solntsev KM, Bartolo E.-A, Pan G, Muller G, Bommireddy S, Huppert D, Tolbert LM. Isr. J. Chem. 2009; 49: 227
• 14 Ayad S, Posey V, Das A, Montgomery JM, Hanson K. Chem. Commun. 2019; 55: 1263

Reviews on glycosylation:
• 15a Sangwan R, Mandal PK. RSC Adv. 2017; 7: 26256
• 15b Nielsen MM, Pedersen CM. Chem. Rev. 2018; 118: 8285
• 15c Kulkarni SS, Wang C.-C, Sabbavarapu NM, Podilapu AR, Liao P.-H, Hung S.-C. Chem. Rev. 2018; 118: 8025
• 16 Iwata R, Uda K, Takahashi D, Toshima K. Chem. Commun. 2014; 50: 10695
• 17 Kimura T, Eto T, Takahashi D, Toshima K. Org. Lett. 2016; 18: 3190

Reviews on hydrogen bond donor catalysis:
• 18a Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520
• 18b Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
• 18c Nagorny P, Sun Z. Beilstein J. Org. Chem. 2016; 12: 2834
• 19 Jakab G, Tancon C, Zhang Z, Lippert KM, Schreiner PR. Org. Lett. 2012; 14: 1724
• 20 This shift in acidity is based on glucosyl trichloroacetimidate activation, which requires a pKa value of ≤ 5 at room temperature.
• 21 Liu J, Yin S, Wang H, Li H, Ni G. Carbohydr. Res. 2020; 490: 107963
• 22 Zhao G, Wang T. Angew. Chem. Int. Ed. 2018; 57: 6120
• 23 Wang T, Li J, Zhao G. Synlett 2020; 31: 823
• 24 Yan D.-M, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2019; 58: 378
• 25 Fukuzumi S, Kotani H, Ohkubo K, Ogo S, Tkachenko NV, Lemmetyinen H. J. Am. Chem. Soc. 2004; 126: 1600
• 26 Iibuchi N, Eto T, Aoyagi M, Kurinami R, Sakai H, Hasobe T, Takahashi D, Toshima K. Org. Biomol. Chem. 2020; 18: 851
• 27a Nishikubo Y, Kanzaki S, Matsumura S, Toshima K. Tetrahedron Lett. 2006; 47: 8125
• 27b Dharpure PD, Bhowmick A, Warghude PK, Bhat RG. Tetrahedron Lett. 2020; 61: 151407
• 28 Yi H, Niu L, Wang S, Liu T, Singh AK, Lei A. Org. Lett. 2017; 19: 122
• 29 Zhou Q, Jia T, Li X.-X, Zhou L, Li C.-J, Feng Y.-S. Synth. Commun. 2018; 48: 1068
• 30 Spiliopoulou N, Nikitas NF, Kokotos CG. Green Chem. 2020; 22: 3539
• 31 de Lijser HJ. P, Rangel NA. J. Org. Chem. 2004; 69: 8315
• 32 Yu L, Lin C, Liao C, Zeng X, Chen X, Zhu Z, Huang Y, Li Y, Chen L. Environ. Chem. Lett. 2020; 18: 1353

Reviews on C–C bond formation:
• 33a Devdutt C, Nabin CB. Curr. Org. Synth. 2012; 9: 17
• 33b Chen F, Wang T, Jiao N. Chem. Rev. 2014; 114: 8613
• 33c Brahmachari G. RSC Adv. 2016; 6: 64676
• 33d Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
• 34 Salem ZM, Saway J, Badillo JJ. Org. Lett. 2019; 21: 8528
• 35 Strada A, Fredditori M, Zanoni G, Protti S. Molecules 2019; 24: 1318