Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide

Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.

Key words

organoselenium catalysis - aza-Wacker reaction - C–H amination - hydrazones - isoquinoline derivatives

• References and Notes


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• 18 Aza-Wacker Reaction; General Procedure To an oven-dried 20 mL vial were added substrate 1 (0.10 mmol), PhSeSePh (3.1 mg, 10 mol%), NFSI (0.12 mmol, 1.2 equiv), and MeCN (4 mL). The mixture was stirred at room temperature for 12 h. After the reaction was complete, the resulting mixture was concentrated under reduced pressure. The residue was directly purified by column chromatography on silica gel to give the corresponding product 2. (3-Phenylisoquinolin-2-ium-2-yl)(tosyl)amide (2e) The crude residue was purified by flash column chromatography on silica gel (eluent: CH₂Cl₂/MeOH, 80:1, v/v) to give 2e as a white solid (35.7 mg, 97% yield). This product is known and its spectra are in accordance with those reported in the literature, see: Wu C., Wang Q., Zhao J., Li P., Shi F.; Synthesis 2012, 44, 3033. ¹H NMR (400 MHz, CDCl₃): δ = 9.70 (s, 1 H), 8.16 (d, J = 8.3 Hz, 1 H), 7.93 (d, J = 3.7 Hz, 2 H), 7.85–7.77 (m, 2 H), 7.37–7.28 (m, 3 H), 7.25–7.19 (m, 2 H), 7.03 (d, J = 8.1 Hz, 2 H), 6.78 (d, J = 8.1 Hz, 2 H), 2.27 (s, 3 H); ¹³C NMR (101 MHz, CDCl₃): δ = 150.83, 148.67, 140.43, 139.99, 135.48, 134.67, 132.35, 130.33, 130.10, 129.19, 128.90, 128.75, 127.65, 127.35, 126.77, 126.52, 125.84, 21.42.
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