Metal-Loaded Semiconductor-Photocatalysis of Alcohols for Selective Organic Synthesis: A Personal Account

Shogo Mori; Shu Sakurai; Hiroshi Naka; Susumu Saito

doi:10.1055/a-2124-4037

Synlett, Table of Contents

Synlett 2023; 34(20): 2361-2373
DOI: 10.1055/a-2124-4037

account

Special Issue Dedicated to Prof. Hisashi Yamamoto

Metal-Loaded Semiconductor-Photocatalysis of Alcohols for Selective Organic Synthesis: A Personal Account

Authors

Shogo Mori∗

^aIntegrated Research Consortium on Chemical Sciences (IRCCS), Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan
Shu Sakurai

^bGraduate School of Science, Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan
Hiroshi Naka ∗

^cGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

^dDeuterium Science Research Unit, Center for the Promotion of Interdisciplinary Education and Research, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
Susumu Saito ∗

^aIntegrated Research Consortium on Chemical Sciences (IRCCS), Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan

^bGraduate School of Science, Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan

Abstract

All articles of this category

Dedicated to Professor Hisashi Yamamoto on the occasion of his 80th birthday

Abstract

In this account, we review our research over the last decade on metal-loaded semiconductor-photocatalyzed organic transformations using alcohols. Different from many reactions using alcohols as mere sacrificial electron donors, our study has demonstrated alcohols as useful organic building blocks incorporated into value-added products. Besides such recollections of previous results, we briefly introduce our ongoing project involving photocatalytic C–C bond-forming reactions via the C–C bond scission of tertiary alcohols.

1 Introduction

2 Dehydroxylative Hydrogenolysis of Allylic Alcohols

3 Acceptorless Dehydrogenation of Activated/Unactivated Alcohols

4 N-Alkylation of Amines using Alcohols as Alkylating Agents

5 Summary and Outlook

Key words

semiconductors - photocatalysts - alcohols - dehydroxylative hydrogenolysis - dehydrogenation - N-alkylation - N-methylation - β-scission

Full Text

References

References
1 Hoffmann MR, Martin ST, Choi W, Bahnemann DW. Chem. Rev. 1995; 95: 69
2 Wenderich K, Mul G. Chem. Rev. 2016; 116: 14587
3 Khlyustova A, Sirotkin N, Kusova T, Kraev A, Titov V, Agafonov A. Mater. Adv. 2020; 1: 1193
4 Fujishima A, Honda K. Nature 1972; 238: 37
5 Kudo A, Miseki Y. Chem. Soc. Rev. 2009; 38: 253
6 Wang Q, Domen K. Chem. Rev. 2020; 120: 919
7 Yoshino S, Takayama T, Yamaguchi Y, Iwase A, Kudo A. Acc. Chem. Res. 2022; 55: 966
8 Nahar S, Zain MF. M, Kadhum AA. H, Hasan HA, Hasan MR. Materials 2017; 10: 629
9 Koe WS, Lee JW, Chong WC, Pang YL, Sim LC. Environ. Sci. Pollut. Res. 2020; 27: 2522
10 Hong J, Cho K.-H, Presser V, Su X. Curr. Opin. Green Sustainable Chem. 2022; 36: 100644
11 Morikawa T, Sato S, Sekizawa K, Suzuki TM, Arai T. Acc. Chem. Res. 2022; 55: 933
12 Nishiyama H, Yamada T, Nakabayashi M, Maehara Y, Yamaguchi M, Kuromiya Y, Nagatsuma Y, Tokudome H, Akiyama S, Watanabe T, Narushima R, Okunaka S, Shibata N, Takata T, Hisatomi T, Domen K. Nature 2021; 598: 304
13 Mori S, Saito S. Green Chem. 2021; 23: 3575
14 Park S, Jeong J, Fujita K, Yamamoto A, Yoshida H. J. Am. Chem. Soc. 2020; 142: 12708
15 Pieber B, Malik JA, Cavedon C, Gisbertz S, Savateev A, Cruz D, Heil T, Zhang G, Seeberger PH. Angew. Chem. Int. Ed. 2019; 58: 9575
16 Ghosh I, Khamrai J, Savateev A, Shlapakov N, Antonietti M, König B. Science 2019; 365: 360
17 Manley DW, McBurney RT, Miller P, Howe RF, Rhydderch S, Walton JC. J. Am. Chem. Soc. 2012; 134: 13580
18 Pitre SP, Scaiano JC, Yoon TP. ACS Catal. 2017; 7: 6440
19 Gisbertz S, Pieber B. ChemPhotoChem 2020; 4: 456
20 Riente P, Noël T. Catal. Sci. Technol. 2019; 9: 5186
21 Parrino F, Bellardita M, García-López EI, Marcì G, Loddo V, Palmisano L. ACS Catal. 2018; 8: 11191
22 Henkel T, Brunne RM, Müller H, Reichel F. Angew. Chem. Int. Ed. 1999; 38: 643
23 Ertl P, Schuhmann T. J. Nat. Prod. 2019; 82: 1258
24 Ohtani B, Osaki H, Nishimoto S, Kagiya T. J. Am. Chem. Soc. 1986; 108: 308
25 Ohtani B, Kakimoto M, Nishimoto S, Kagiya T. J. Photochem. Photobiol., A 1993; 70: 265
26 Stroyuk OL, Kuchmy SY. Theor. Exp. Chem. 2020; 56: 143
27 Ma D, Zhai S, Wang Y, Liu A, Chen C. Molecules 2019; 24: 330
28 Caner J, Liu Z, Takada Y, Kudo A, Naka H, Saito S. Catal. Sci. Technol. 2014; 4: 4093
29 Takada Y, Caner J, Kaliyamoorthy S, Naka H, Saito S. Chem. Eur. J. 2017; 23: 18025
30 Takada Y, Caner J, Naka H, Saito S. Pure Appl. Chem. 2018; 90: 167
31 Ruberu TP. A, Nelson NC, Slowing II, Vela J. J. Phys. Chem. Lett. 2012; 3: 2798
32 Fu H, Chen H, Gao B, Lu T, Su Y, Zhou L, Liu M, Li H, Yang X. ChemCatChem 2022; 14,: 202200120
33 Shiraishi Y, Fujiwara K, Sugano Y, Ichikawa S, Hirai T. ACS Catal. 2013; 3: 312
34 Sasaki Y, Nemoto H, Saito K, Kudo A. J. Phys. Chem. C 2009; 113: 17536
35 Sasaki Y, Iwase A, Kato H, Kudo A. J. Catal. 2008; 259: 133
36 Liu Z, Caner J, Kudo A, Naka H, Saito S. Chem. Eur. J. 2013; 19: 9452
37 Yamauchi M, Saito H, Sugimoto T, Mori S, Saito S. Coord. Chem. Rev. 2022; 472: 214773
38 Shibata M, Nagata R, Saito S, Naka H. Chem. Lett. 2017; 46: 580
39 Qi M.-Y, Conte M, Anpo M, Tang Z.-R, Xu Y.-J. Chem. Rev. 2021; 121: 13051
40 Zhao L.-M, Meng Q.-Y, Fan X.-B, Ye C, Li X.-B, Chen B, Ramamurthy V, Tung C.-H, Wu L.-Z. Angew. Chem. Int. Ed. 2017; 56: 3020
41 Imamura K, Tsukahara H, Hamamichi K, Seto N, Hashimoto K, Kominami H. Appl. Catal., A 2013; 450: 28
42 Reed-Berendt BG, Latham DE, Dambatta MB, Morrill LC. ACS Cent. Sci. 2021; 7: 570
43 Kabadwal LM, Bera S, Banerjee D. Org. Chem. Front. 2021; 8: 7077
44 Barreiro EJ, Kümmerle AE, Fraga CA. M. Chem. Rev. 2011; 111: 5215
45 Tsarev VN, Morioka Y, Caner J, Wang Q, Ushimaru R, Kudo A, Naka H, Saito S. Org. Lett. 2015; 17: 2530
46 Wang L.-M, Jenkinson K, Wheatley AE. H, Kuwata K, Saito S, Naka H. ACS Sustainable Chem. Eng. 2018; 6: 15419
47 Wang L.-M, Kobayashi K, Arisawa M, Saito S, Naka H. Org. Lett. 2019; 21: 341
48 Chen W, Fu X, Liu X, Ye L, Yuan Y. Mol. Catal. 2023; 538: 112993
49 Wang L.-M, Morioka Y, Jenkinson K, Wheatley AE. H, Saito S, Naka H. Sci. Rep. 2018; 8: 6931
50 Hashiba Y, Mori S, Huang I, Morioka Y, Naka H, Saito S. Asian J. Org. Chem. 2023; e202300230 DOI:
51 Yu Q, Shi X, Greer T, Lietz CB, Kent KC, Li L. J. Proteome Res. 2016; 15: 3420
52 Kim J, Lee H, Yi S.-J, Kim K. Exp. Mol. Med. 2022; 54: 878
53 Dawson PE. Isr. J. Chem. 2011; 51: 862
54 Zhang L, Zhang Y, Deng Y, Shi F. Catal. Sci. Technol. 2015; 5: 3226
55 Stíbal D, Sá J, van Bokhoven JA. Catal. Sci. Technol. 2013; 3: 94
56 Zhang L, Zhang Y, Deng Y, Shi F. RSC Adv. 2015; 5: 14514
57 Wang B, Deng Z, Fu X, Xu C, Li Z. Appl. Catal., B 2018; 237: 970
58 Wada Y, Akiyama T, Harada K, Honma T, Naka H, Saito S, Arisawa M. RSC Adv. 2021; 11: 22230
59 Courtois C, Eder M, Schnabl K, Walenta CA, Tschurl M, Heiz U. Angew. Chem. Int. Ed. 2019; 58: 14255
60 Walenta CA, Kollmannsberger SL, Courtois C, Tschurl M, Heiz U. Phys. Chem. Chem. Phys. 2018; 20: 7105
61 Zhu Q, Nocera DG. J. Am. Chem. Soc. 2020; 142: 17913
62 Aynetdinova D, Callens MC, Hicks HB, Poh CY. X, Shennan BD. A, Boyd AM, Lim ZH, Leitch JA, Dixon DJ. Chem. Soc. Rev. 2021; 50: 5517
63 Liu P, Xue G, Lai Y, Li Y, Chen X, Guo Q. J. Phys. Chem. C 2022; 126: 3457
64 Bi X, Du G, Kalam A, Sun D, Yu Y, Su Q, Xu B, Al-Sehemi AG. Chem. Eng. Sci. 2021; 234: 116440
65 Lee J, Choi W. Environ. Sci. Technol. 2004; 38: 4026
66 Wada E, Takeuchi T, Fujimura Y, Tyagi A, Kato T, Yoshida H. Catal. Sci. Technol. 2017; 7: 2457
67 Coronado JM, Zorn ME, Tejedor-Tejedor I, Anderson MA. Appl. Catal., B 2003; 43: 329
68 Suda Y, Morimoto T, Nagao M. Langmuir 1987; 3: 99
69 Sato H, Ishikawa A, Saito H, Higashi T, Takeyasu K, Sugimoto T. Commun. Chem. 2023; 6: 8
70 Ooi T, Miura T, Maruoka K. J. Am. Chem. Soc. 1998; 120: 10790
71 Ooi T, Miura T, Ohmatsu K, Saito A, Maruoka K. Org. Biomol. Chem. 2004; 2: 3312