Radical Cation [2+2] Cycloadditions Enabled by Surface-Assisted Pseudo-Intramolecular Electron Transfers

Sota Adachi; Naoya Maeta; Kaii Nakayama; Zimo Wang; Yasuhiro Hashimoto; Yohei Okada

doi:10.1055/a-2039-4825

Synthesis, Table of Contents

Synthesis 2023; 55(18): 3013-3018
DOI: 10.1055/a-2039-4825

paper

Special Issue Electrochemical Organic Synthesis

Radical Cation [2+2] Cycloadditions Enabled by Surface-Assisted Pseudo-Intramolecular Electron Transfers

Sota Adachi

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Naoya Maeta

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Kaii Nakayama

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Zimo Wang

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Yasuhiro Hashimoto

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Yohei Okada ∗

^aDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

Both intermolecular and intramolecular electron transfers can be the key in the determination of synthetic outcomes of photochemical and electrochemical reactions. Herein, we report dispersed TiO₂ nanoparticles in combination with methoxybenzene to be a unique heterogeneous photocatalyst for facilitating the formation of novel cyclobutanes. Although the mechanistic details are as yet unclear, the results described herein imply that methoxybenzene is adsorbed onto the TiO₂ surface, coming in close proximity to the forming cyclobutane radical cation, to realize a pseudo-intramolecular electron transfer between the species.

Key words

radical cations - [2+2] cycloaddition - surface-assisted - pseudo-intramolecular process - electron transfer

Full Text

References

References

For selected reviews, see:

1a Silvi M, Melchiorre P. Nature 2018; 554: 41
1b Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
1c Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
1d Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
1e Kärkäs MD, Porco JA. Jr, Stephenson CR. J. Chem. Rev. 2016; 116: 9683
1f Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322

For selected reviews, see:

2a Rafiee M, Mayer MN, Punchihewa BT, Mumau MR. J. Org. Chem. 2021; 86: 15866
2b Little RD. J. Org. Chem. 2020; 85: 13375
2c Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786
2d Möhle S, Zirbes M, Rodrigo E, Gieshoff T, Wiebe A, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 6018
2e Wiebe A, Gieshoff T, Möhle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594
2f Waldvogel SR, Lips S, Selt M, Riehl B, Kampf CJ. Chem. Rev. 2018; 118: 6706
2g Moeller KD. Chem. Rev. 2018; 118: 4817
2h Nutting JE, Rafiee M, Stahl SS. Chem. Rev. 2018; 118: 4834
2i Yoshida J, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702
2j Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
2k Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230

For selected reviews, see:

3a Huang H.-M, Garduño-Castro MH, Morrill C, Procter DJ. Chem. Soc. Rev. 2019; 48: 4626
3b Matsui JK, Lang SB, Heitz DR, Molander GA. ACS Catal. 2017; 7: 2563
3c Yan M, Lo JC, Edwards JT, Baran PS. J. Am. Chem. Soc. 2016; 138: 12692
3d Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
3e Hoffmann RW. Chem. Soc. Rev. 2016; 45: 577
3f Chen Z.-M, Zhang X.-M, Tu Y.-Q. Chem. Soc. Rev. 2015; 44: 5220
3g Zhang B, Studer A. Chem. Soc. Rev. 2015; 44: 3505
3h Tang S, Liu K, Liu C, Lei A. Chem. Soc. Rev. 2015; 44: 1070
3i Wille U. Chem. Rev. 2013; 113: 813

4 Feng R, Smith JA, Moeller KD. Acc. Chem. Res. 2017; 50: 2346

5a Nacsa ED, MacMillan DW. C. J. Am. Chem. Soc. 2018; 140: 3322
5b Jin J, MacMillan DW. C. Nature 2015; 525: 87

6a Cao Z.-Y, Ghosh T, Melchiorre P. Nat. Commun. 2018; 9: 3274
6b Bahamonde A, Murphy JJ, Savarese M, Bremond E, Cavalli A, Melchiorre P. J. Am. Chem. Soc. 2017; 139: 4559
6c Murphy JJ, Bastida D, Paria S, Fagnoni M, Melchiorre P. Nature 2016; 532: 218

For recent examples, see:

7a Adachi S, Horiguchi G, Kamiya H, Okada Y. Eur. J. Org. Chem. 2022; e202201207
7b Hashimoto Y, Horiguchi G, Kamiya H, Okada Y. Chem. Eur. J. 2022; 28: e202202018
7c Nakayama K, Kamiya H, Okada Y. Beilstein J. Org. Chem. 2022; 18: 1100
7d Maeta N, Kamiya H, Okada Y. J. Org. Chem. 2020; 85: 6551
7e Nakayama K, Maeta N, Horiguchi G, Kamiya H, Okada Y. Org. Lett. 2019; 21: 2246
7f Okada Y, Maeta N, Nakayama K, Kamiya H. J. Org. Chem. 2018; 83: 4948

For selected reviews, see:

8a Okada Y. Electrochemistry 2020; 88: 497
8b Okada Y, Chiba K. Chem. Rev. 2018; 118: 4592

9a Shida N, Imada Y, Okada Y, Chiba K. Eur. J. Org. Chem. 2020; 570
9b Imada Y, Yamaguchi Y, Shida N, Okada Y, Chiba K. Chem. Commun. 2017; 53: 3960

10 Okada Y. Chem. Rec. 2021; 21: 2223

11a Okada Y. J. Org. Chem. 2019; 84: 1882
11b Okada Y, Yamaguchi Y, Ozaki A, Chiba K. Chem. Sci. 2016; 7: 6387
11c Okada Y, Nishimoto A, Akaba R, Chiba K. J. Org. Chem. 2011; 76: 3470

12a Maeta N, Kamiya H, Okada Y. Org. Lett. 2019; 21: 8519
12b Yamaguchi Y, Okada Y, Chiba K. J. Org. Chem. 2013; 78: 2626

13 Tanami S, Hussaini SR, Kitano Y, Chiba K, Okada Y. Eur. J. Org. Chem. 2022; e202201023

For selected reviews of the alkene-derived radical cation chemistry, see:

14a Luo M.-J, Xiao Q, Li J.-H. Chem. Soc. Rev. 2022; 51: 7206
14b Margrey KA, Nicewicz DA. Acc. Chem. Res. 2016; 49: 1997

15a Colomer I, Chamberlain AE. R, Haughey MB, Donohoe TJ. Nat. Rev. Chem. 2017; 1: 0088
15b Eberson L, Hartshorn MP, Persson O, Radner F. Chem. Commun. 1996; 2105

Supplementary Material

Supporting Information