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Synlett 2022; 33(12): 1194-1198
DOI: 10.1055/a-1665-9220
cluster
Organic Photoredox Catalysis in Synthesis – Honoring Prof. Shunichi Fukuzumi’s 70th Birthday

Red-Light-Induced N,N′-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

Savannah M. Stull
a   Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721, USA
,
Liangyong Mei
b   Department of Chemistry, Colgate University, 13 Oak Dr, Hamilton, NY 13346, USA
,
Thomas L. Gianetti  ∗
a   Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721, USA
› InstitutsangabenWe are grateful to the University of Arizona and the ACS Petroleum Research Fund (grant no. 59631-DNI3) for financially supporting this work. All NMR data were collected in the NMR facility of the Department of Chemistry and Biochemistry at the University of Arizona, and we thank Dr. Jixun Dai for his help. The purchase of the Bruker NEO 500 MHz spectrometer was supported by the National Science Foundation (Grant No. 1920234) and by the University of Arizona.
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Abstract

A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N′-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obtained in moderate to excellent yields under mild conditions.

Key words

photoredox catalysis - [3+2] cycloaddition - cyclopropylamines - alkenes - alkynes - dipropyldimethoxyquinacridinium

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1665-9220. Included are general information, substrate synthesis and characterization, mechanistic investigation, experimental procedures, as well as NMR spectroscopy data.
  • Supporting Information


Publikationsverlauf

Eingereicht: 26. August 2021

Angenommen nach Revision: 10. Oktober 2021

Accepted Manuscript online:
10. Oktober 2021

Artikel online veröffentlicht:
12. November 2021

© 2021. Thieme. All rights reserved

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  • 17 Red-Light-Induced nPr-DMQA+-Catalyzed [3+2] Cycloaddition of N-Cyclopropylanilines 1 with Alkenes 2; General Procedure In a N2 glove box, an oven-dried (overnight) Schlenk tube containing a stirring bar was charged with the appropriate substrate 1 (0.2 mmol, 1.0 equiv) and alkene 2 (1.0 mmol, 1.2 equiv). This was followed by the addition of [nPr-DMQA+][BF4 –] (1.0 mg, 0.002 mmol, 1.0 mol%) in degassed MeNO2 (1 mL), transferred from a stock solution of the catalyst (10.0 mg) in degassed MeNO2 (10 mL). The Schlenk tube was then sealed and removed from the glove box, and the solution was stirred at rt under red LED (λmax = 640 nm) irradiation until the reaction was complete. The mixture was then concentrated under reduced pressure on a rotary evaporator, and the crude product was purified by flash chromatography (FC) [silica gel, hexanes–Et2O or EtOAc (200:1 to 6:1)]. trans-N-(2-Phenylcyclopentyl)aniline (3a-I) 10c Colorless oil; yield: 20 mg (42%). Rf = 0.3 (hexanes–EtOAc, 20:1). FC: hexanes–Et2O (99:1). 1H NMR (500 MHz, CDCl3): δ = 7.31 (dd, J = 8.0, 8.0 Hz, 2 H, ArH), 7.25–7.21 (m, 3 H, ArH), 7.12 (dd, J = 8.0, 8.0 Hz, 2 H, ArH), 6.65 (dd, J = 8.0, 8.0 Hz, 1 H, ArH), 6.48 (d, J = 8.0 Hz, 2 H, ArH), 4.01 (dd, J = 12.0, 6.0 Hz, 1 H, CH), 3.46 (dd, J = 15.0, 7.5 Hz, 1 H, CH), 3.37 (bs, 1 H, NH), 2.22–2.07 (m, 3 H, CH2), 2.02–1.94 (m, 1 H, CH2), 1.89–1.76 (m, 2 H, CH2). 13C NMR (126 MHz, CDCl3): δ = 147.91, 140.84, 129.18, 128.77, 128.43, 126.59, 117.01, 113.32, 57.57, 48.15, 32.01, 28.94, 22.19. cis-N-(2-Phenylcyclopentyl)aniline (3a-II) 10c Colorless oil; yield: 2 mg, 46%; Rf = 0.2 (hexanes–EtOAc, 20:1). FC: hexanes–Et2O (99:1). 1H NMR (500 MHz, CDCl3): δ = 7.34–7.28 (m, 4 H, ArH), 7.22 (dd, J = 7.5, 7.5 Hz, 1 H, ArH), 7.13 (dd, J = 7.5, 7.5 Hz, 2 H, ArH), 6.67 (dd, J = 7.5, 7.5 Hz, 1 H, ArH), 6.55 (d, J = 7.5 Hz, 2 H, ArH), 3.80 (bs, 1 H, NH), 3.80 (dd, J = 13.0, 7.0 Hz, 1 H, CH), 2.93 (dd, J = 17.0, 8.0 Hz, 1 H, CH), 2.38 (ddd, J = 21.0, 14.5, 7.5 Hz, 1 H, CH2), 2.26–2.19 (m, 1 H, CH2), 1.94–1.82 (m, 2 H, CH2), 1.81–1.75 (m, 1 H, CH2), 1.66–1.58 (m, 1 H, CH2). 13C NMR (126 MHz, CDCl3): δ = 148.16, 143.83, 129.25, 128.69, 127.48, 126.54, 117.19, 113.47, 61.58, 53.27, 33.59, 33.55, 23.46.