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Synlett 2024; 35(09): 1019-1022
DOI: 10.1055/a-2204-9522
DOI: 10.1055/a-2204-9522
cluster
Chemical Synthesis and Catalysis in Germany
Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels–Alder Reaction of Phthalazines and Cyclooctynes
The authors acknowledge the LOEWE Program of Excellence of the Federal State of Hesse (LOEWE Focus Group PriOSS ‘Principles of On-Surface Synthesis’) for financial support.
Abstract
Herein we report a method for facilitating the inverse-electron-demand Diels–Alder reaction of 1,2-diazines and cyclooctynes by utilizing a boron-based bidentate Lewis acid catalyst. Readily available electron-deficient and electron-rich phthalazines proved to be suitable substrates in this transformation. The described method enables the facile construction of diversely substituted polycyclic aromatic hydrocarbons fused to eight-membered carbocycles.
Key words
cycloaddition - diazines - cyclooctyne - bidentate catalysis - polycyclic aromatic hydrocarbons - Diels–Alder reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2204-9522.
- Supporting Information
Publication History
Received: 15 October 2023
Accepted after revision: 06 November 2023
Accepted Manuscript online:
06 November 2023
Article published online:
13 December 2023
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- 19 General procedure for the BDLA-catalyzed IEDDA reaction: In a nitrogen-filled glove box, (substituted) phthalazine 1 (0.10 mmol, 1.0 equiv) and BDLA catalyst (5.0 μmol, 5.0 mol%) were suspended in anhydrous and degassed 1,4-dioxane (1.0 mL) in a 4 mL screw-cap vial with a stirrer bar. Cyclooctyne (2) or exo-BCN (1.1–3.0 equiv) was added to the mixture, and the vial was sealed and taken out of the glove box. The mixture was stirred at the given temperature for the given time. Afterwards, the reaction mixture was concentrated in vacuo. The ratio of product to unreacted phthalazine was determined by 1H NMR spectroscopic analysis of the crude mixture. The crude mixture was purified by column chromatography (3 g of silica gel) to afford product 3 or 4
- 20 ((1r,1aR,11aS)-1a,2,3,10,11,11a-hexahydro-1H-cyclopropa[5,6]cycloocta[1,2-b]naphthalen-1-yl)methanol (4a): Yield: 13 mg (52%); colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.76–7.71 (m, 2 H), 7.56 (s, 2 H), 7.41–7.36 (m, 2 H), 3.38 (d, J = 6.5 Hz, 2 H), 3.10 (ddd, J = 14.1, 8.3, 5.7 Hz, 2 H), 2.92 (dt, J = 14.1, 5.8 Hz, 2 H), 2.59–2.45 (m, 2 H), 1.42–1.25 (m, 3 H), 0.77–0.66 (m, 3 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 141.21 (2 C), 132.49 (2 C), 128.04 (2 C), 127.08 (2 C), 125.24 (2 C), 66.78, 33.63 (2 C), 30.16 (2 C), 29.76 (2 C), 22.03. HRMS (ESI): m/z calcd for C18H20ONa: 275.1406 [M + Na]+; found: 275.1406.