Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water

Yuki Hyodo; Keigo Takahashi; Youhei Chitose; Manabu Abe; Michito Yoshizawa; Takashi Koike; Munetaka Akita

doi:10.1055/a-1652-2707

Synlett, Table of Contents

Synlett 2022; 33(12): 1184-1188
DOI: 10.1055/a-1652-2707

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Organic Photoredox Catalysis in Synthesis – Honoring Prof. Shunichi Fukuzumi’s 70th Birthday

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water

Yuki Hyodo

^aSchool of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan

,

Keigo Takahashi

^aSchool of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan

,

Youhei Chitose

^bDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima, 739-8526, Japan

,

Manabu Abe

^bDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima, 739-8526, Japan

,

Michito Yoshizawa

^cLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan

,

Takashi Koike ∗

^dDepartment of Applied Chemistry, Faculty of Fundamental Engineering, Nippon Institute of Technology, 4-1 Gakuendai, Miyashiro-machi, Saitama, 345-8501, Japan

,

Munetaka Akita∗

^aSchool of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan

^cLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan

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Abstract

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Abstract

Host–guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m-phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.

Key words

photoredox catalysis - supramolecular catalysts - organophotocatalysis - radical reaction - Weinreb amides - demethoxylation

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References

References and Notes

For selected recent references on photoredox catalysis, see:

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9 CCDC 2097141 contains the supplementary crystallographic data for compound 1c. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
10 Photocatalytic Demethoxylation of Weinreb Amides: General Procedure A 4 mL sample bottle was charged with amide 4 (0.13 mmol), Et₃N (0.26 mmol), and 1.3 mM aq 3c (2 mL, 2 mol%), and then placed 1 cm away from blue LED lamps (λ = 425 nm). The mixture was irradiated, with stirring and cooling by a fan for 3–48 h. H₂O (5 mL) was then added and the resulting mixture was extracted with CH₂Cl₂ (3 × 15 mL). The organic layer was dried (Na₂SO₄) and concentrated, and the crude product was purified by gel-permeation chromatography. N,4-Dimethylbenzamide (5a) White solid; yield: 16.3 mg (88%, 0.109 mmol). ¹H NMR (400 MHz, CDCl₃): δ = 7.65 (d, J = 8.0 Hz, 2 H, Ar), 7.22 (d, J = 8.0 Hz, 2 H, Ar), 6.10 (br s, 1 H, NH), 3.00 (d, J = 4.7 Hz, 3 H, CH ₃), 2.39 (s, 3 H, CH ₃). N-Methylbiphenyl-4-carboxamide (5c) White solid; yield: 20.0 mg (69%, 0.0904 mmol). ¹H NMR (400 MHz, CDCl₃): δ = 7.84 (d, J = 8.3 Hz, 2 H, Ar), 7.65–7.59 (m, 4 H, Ar), 7.46 (dd, J = 7.1, 7.7 Hz, 2 H, Ar), 7.38 (t, J = 7.4 Hz, 1 H, Ar), 6.28 (br s, 1 H, NH), 3.04 (d, J = 4.8 Hz, 3 H, CH ₃).
11 Cutulic S, Murphy J, Farwaha H, Zhou S.-Z, Chrystal E. Synlett 2008; 2132
12 Quenching experiments for 3c with quenchers 4a and Et₃N in water showed a significant increase in fluorescence intensity. In addition, 4a affected the lifetime of the fluorescent excited species. These results also suggest that unique assemblies are formed in the present system (see the Supporting Information).

Supplementary Material

Supporting Information