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Synlett 2013; 24(16): 2148-2152
DOI: 10.1055/s-0033-1339640
DOI: 10.1055/s-0033-1339640
letter
Cationic Iron(III) Porphyrin Catalyzed Dehydrative Friedel–Crafts Reaction of Alcohols with Arenes
Further Information
Publication History
Received: 04 July 2013
Accepted after revision: 18 July 2013
Publication Date:
28 August 2013 (online)
Abstract
Alcohols react with arenes in the presence of cationic iron(III) porphyrin catalyst. The reaction involves the formation of the C–C bond via dehydration, which is formal Lewis acid catalyzed Friedel–Crafts reaction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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- 7 General Procedure for the Dehydrative Friedel–Crafts Reaction of Alcohols with Arenes To a screw-cap vial was added [Fe(TPP)][SbF6] (0.02 mmol, 18 mg), followed by the alcohol (0.4 mmol), the arene (2 mmol), and dry 1,2-DCE (1.0 mL) in a dry box. The vial was sealed and stirred at 80 °C for 5 h. The reaction mixture was diluted with hexane–EtOAc (10:1), passed through a short silica gel pad and washed with hexane–EtOAc (1:1), concentrated in vacuo. The crude product was purified by flash column chromatography using SiO2 (hexane–EtOAc). Selected Data for Compound 3aa Yield: 72%; colorless oil. TLC: Rf = 0.62 (hexane–toluene, 2:1). 1H NMR (500 MHz, CDCl3): δ = 7.36 (d, J = 7.5 Hz, 2 H), 7.31–7.28 (m, 2 H), 7.22–7.16 (m, 3 H), 6.88–6.86 (m, 1 H), 6.44 (d, J = 16.0 Hz, 1 H), 6.38–6.32 (m, 1 H), 3.81 (s, 3 H), 3.50 (d, J = 6.5 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 158.1, 137.5, 132.2, 130.7, 129.7, 129.6, 128.5, 127.0, 126.1, 113.9, 55.3, 38.4. IR (neat): 3025, 1511, 1246, 1175, 1035, 966, 827, 729, 692 cm–1. MS: m/z (%) = 224/25 (100/17) [M+]. HRMS (APCI): m/z [M + H]+ calcd for C16H16O: 225.1274; found: 225.1269.
For some recent reviews on Friedel–Crafts reaction, see:
For examples of the use of metalloporphyrins in nonoxidative bond formation, see: