Nickel-Catalyzed α-1,3-Dienylation of 1,3-Dicarbonyl Compounds with Propargylic Carbonates

Abstract

Herein reported is a nickel-catalyzed α-1,3-dienylation reaction of 1,3-dicarbonyl compounds with substituted propargylic (e.g., but-2-ynyl) carbonates. The propargyl unit changes into a 1,3-dienyl unit, which is incorporated at the α-position of the 1,3-dicarbonyl compounds.

Key words

nickel - 1,3-diene - malonate - propargylic carbonate - C–C bond formation

Publikationsverlauf

Eingereicht: 15. September 2020

Angenommen nach Revision: 05. Oktober 2020

Accepted Manuscript online:
05. Oktober 2020

Artikel online veröffentlicht:
02. November 2020

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• 14 α-Dienylation of Malonate 1 with 2: Typical Procedure Ni(cod)₂ (5.5 mg, 0.020 mmol, 5 mol%) and ligand 5 (15.6 mg, 0.030 mmol, 8 mol%) were placed in a vial. Acetonitrile (2 mL) was added, and the mixture was stirred at room temperature for 5 min. Then, malonate 1 (69.7 mg, 0.40 mmol) and propargyl carbonate 2 (88.5 mg, 0.52 mmol, 1.3 equiv) were added to the mixture, which was stirred at 80 °C for 24 h. After cooled to room temperature, the reaction mixture was passed through a pad of silica gel, which was eluted with ethyl acetate. The filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative thin-layer chromatography (PTLC; eluent: hexane/ethyl acetate = 10:1) to give a colorless oil (80.4 mg), which was estimated by ¹H NMR spectroscopy to contain 3 (0.33 mmol, 81%) and 4 (0.029 mmol, 7%). ¹H NMR (400 MHz, CDCl₃): δ = 1.26 (t, J = 7.0 Hz, 6 H), 1.63 (s, 3 H), 4.22 (q, J = 7.2 Hz, 4 H), 5.02 (s, 1 H), 5.09 (d, J = 10.8 Hz, 1 H), 5.38 (d, J = 17.2 Hz, 1 H), 5.42 (s, 1 H), 6.31 (dd, J = 17.2, 11.2 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 14.1, 21.2, 58.9, 61.7, 114.1, 115.8, 136.2, 145.2, 171.1. HRMS (APCI⁺): m/z calcd for C₁₂H₁₉O₄ [M + H]⁺: 227.1283; found: 227.1279. IR (ATR): 2983, 1728, 1248, 1219, 1101, 1018 cm^–1.