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Synlett 2013; 24(1): 130-134
DOI: 10.1055/s-0032-1317705
DOI: 10.1055/s-0032-1317705
letter
Synthesis of Multisubstituted Indenes via Iron-Catalyzed Domino Reaction of Benzylic Compounds and Alkynes
Authors
Weitere Informationen
Publikationsverlauf
Received: 18. Oktober 2012
Accepted after revision: 07. November 2012
Publikationsdatum:
06. Dezember 2012 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
-
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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.