Synthesis of Multisubstituted Indenes via Iron-Catalyzed Domino Reaction of Benzylic Compounds and Alkynes

Abstract

A novel approach to synthesizing multisubstituted indenes by iron-catalyzed domino reaction of benzylic compounds and alkynes under mild conditions was developed. This system could be applied to various available substrates in a one-step synthetic procedure in moderate to good yields.

Key words

indenes - iron catalysis - domino reaction - one-step procedure - annulation

• References and Notes

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• 11 General Procedure for the Iron-Catalyzed Domino Reaction – Synthesis of 6-Benzhydryl-1,2,3-triphenyl-1H-indene (3aa) Diphenylacetylene 1a (44.5 mg, 0.25 mmol), FeCl₂ (3.1 mg, 10 mmol%), and NBS (97.9 mg, 0.55 mmol) were added to a flask with a magnetic stirring bar. The tube was evacuated and refilled with N₂, and then diphenylmethane (2a, 210 μL, 1.25 mmol) and DCE (2 mL) was added. The resulting mixture was stirred at 80 °C for 10 h. After cooling to r.t., the mixture was diluted with EtOAc and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (PE as eluent) to give product 3aa (75% yield); white solid; mp 155–157 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.40–7.28 (m, 5 H), 7.22–7.13 (m, 8 H), 7.10–6.98 (m, 14 H), 6.98–6.94 (m, 1 H), 5.50 (s, 1 H), 5.03 (s, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 148.4, 145.5, 144.1, 144.0, 143.4, 141.6, 140.4, 139.7, 135.5, 129.4, 129.2, 129.1, 128.6, 128.5, 128.2, 128.1, 127.8, 127.4, 126.5, 126.1, 125.3, 120.1, 57.9, 56.8.