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Synlett 2023; 34(02): 143-148
DOI: 10.1055/a-1946-7691
DOI: 10.1055/a-1946-7691
letter
Photocatalytic Decarboxylative Cyclization of 1,6-Enynes and N-Methacryloyl-2-phenylbenzimidazoles by Potassium Iodide/ Triphenylphosphine Catalysis
Authors
We thank the Fundamental Research Funds for the Provincial Universities of Zhejiang (SJLY2021004), and Education Foundation of Zhejiang Province (Y202146200) for financial support.
Abstract
We describe a photocatalytic decarboxylative cyclization of 1,6-enynes or N-methacryloyl-2-phenylbenzimidazoles for efficient and ecofriendly syntheses of lactams or benzimidazo[2,1-a]isoquinoline-6(5H)-ones, respectively, by the use of KI/PPh3 as a redox catalyst system. In this method, N-hydroxyphthalimide esters were used as alkyl-radical precursors to achieve this decarboxylative cyclization without any dyes, transition-metal catalysts, oxidants, or bases.
Keywords
green chemistry - photocatalysis - transition-metal free - cyclization - lactams - benzimidazoquinolinonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1946-7691.
- Supporting Information (PDF)
Publication History
Received: 04 August 2022
Accepted after revision: 19 September 2022
Accepted Manuscript online:
19 September 2022
Article published online:
21 November 2022
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- 15 Compounds 3a–y; General Procedure A Schlenk tube was charged with the appropriate 1,6-enyne 1 (0.2 mmol), NHPI ester 2 (2 equiv), PPh3 (20 mol%), and KI (1.5 equiv), and the tube was evacuated and filled with N2 three times. DMF (2 mL) was added from a gastight syringe under N2. The mixture in the tube was then stirred at r.t. under 5 W blue LED light for 18 h until the starting material was completely consumed (TLC or GC/MS). The mixture was then extracted with EtOAc (×3), and the organic layers were combined and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, hexane–EtOAc (15:1)]. 3-(Cyclohexylmethyl)-3-methyl-4-methylene-1-phenylpyrrolidin-2-one (3a) Colorless oil; yield: 0.0470 g (83%). 1H NMR (400 MHz, CDCl3): δ = 7.70–7.68 (m, 2 H), 7.41–7.37 (m, 2 H), 7.18–7.14 (m, 1 H), 5.23 (t, J = 2.4 Hz, 1 H), 5.09 (t, J = 2.8 Hz, 1 H), 4.47–4.43 (m, 2 H), 1.86–1.81 (m, 1 H), 1.61–1.52 (m, 8 H), 1.30 (s, 3 H), 1.12–1.07 (m, 2 H), 0.95–0.88 (m, 2 H). 13C NMR (101 MHz, CDCl3): δ = 177.6, 146.0, 139.2, 129.0, 124.6, 119.9, 107.9, 52.0, 49.3, 46.6, 35.1, 34.7, 33.6, 26.9, 26.4, 26.3, 26.2. HRMS (ESI): m/z [M + H]+ calcd for C19H26NO: 284.2009; found: 284.2004.
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For selected papers on the use of organic-dye photocatalysts, see:
For the use of metal-complex photocatalysts, see:
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Two similar synthetic protocols had been reported at the time we were preparing this article: