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Synlett 2021; 32(07): 679-684
DOI: 10.1055/a-1345-3491
letter

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

Ao Li‡
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Bin Pan‡
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
,
Chao Mu
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Na Wang
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
,
Yu-Long Li∗
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Qin Ouyang∗
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
› Author AffiliationsThe National Key R&D program of China (2018YFA0507900), the Chongqing Young Top Talents Training Plan, Chongqing Postdoctoral Innovation Project Funding (cstc2019jcyj-bsh0019), and Sichuan Provincial Human Resource and Social Security Department.
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Abstract

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

Key words

photocatalysis - oxidation - porphyrins - zinc catalysis - dihydroisoquinolones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1345-3491.
  • Supporting Information


Publication History

Received: 03 December 2020

Accepted after revision: 04 January 2021

Accepted Manuscript online:
04 January 2021

Article published online:
18 January 2021

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  • 14 3,4-Dihydroisoquinolin-1(2H)-ones 2a–t; General Procedure The appropriate N-aryltetrahydroquinoline 1 (0.1 mM, 1 equiv), ZnTPP (0.001 mM, 1% equiv, 0.68 mg), and CsF (0.3 mM, 3 equiv, 46 mg) were added to DMF (0.1 M), and the mixture was stirred at rt and irradiated by blue LEDs under air overnight. The mixture was then extracted with CH2Cl2 and the extracts were washed with H2O. The combined organic phases were dried (Na2SO4) and concentrated under reduced pressure, and the crude product was purified by column chromatography (silica gel, PE–EtOAc). 2-Phenyl-3,4-dihydroisoquinolin-1(2H)-one (2a) White solid; yield: 15.8 mg (71%); mp 100–101 °C. 1H NMR (600 MHz, CDCl3): δ = 8.16 (d, J = 7.4 Hz, 1 H), 7.47 (t, J = 7.4 Hz, 1 H), 7.40 (dq, J = 16.8, 8.0 Hz, 5 H), 7.25 (d, J = 10.5 Hz, 2 H), 4.00 (t, J = 6.4 Hz, 2 H), 4.00 (t, 3.15 (t, J = 6.4 Hz, 2 H). 13C NMR (150 MHz, CDCl3): δ = 164.2, 143.1, 138.3, 132.0, 129.7, 128.9, 128.7, 127.2, 126.9, 126.2, 125.3, 49.4, 28.6. HRMS (ESI): m/z [M + Na]+ calcd for C15H13NNaO: 246.0895; found: 246.0889.