Sequential Oxidation–Prins Reaction Processes Induced by the Same Iron Salt: Direct Access to 2-Aryl-4-Chloro-Tetrahydropyrans from Benzyl ­Alcohols

Fabienne Fache; Mickaël Muselli; Olivier Piva

doi:10.1055/s-0033-1339306

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(14): 1781-1784
DOI: 10.1055/s-0033-1339306

letter

Sequential Oxidation–Prins Reaction Processes Induced by the Same Iron Salt: Direct Access to 2-Aryl-4-Chloro-Tetrahydropyrans from Benzyl Alcohols

Fabienne Fache*

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France Fax: +33(4)72448136 eMail: piva@univ-lyon1.fr

,

Mickaël Muselli

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France Fax: +33(4)72448136 eMail: piva@univ-lyon1.fr

,

Olivier Piva*

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France Fax: +33(4)72448136 eMail: piva@univ-lyon1.fr

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Abstract

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Abstract

A clay-supported iron(III) nitrate (Clayfen) was used as a stoichiometric reagent to first oxidize benzylic alcohols. The aldehydes thus obtained were converted in situ into tetrahydropyrans by way of a Prins cyclization induced by iron species already present in the media.

Key words

oxidation - benzyl alcohols - Prins cyclization - sequential reactions - iron catalysis

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Referenzen

References and Notes

1a Tietze LF, Brasche G, Gericke KM In Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
1b Pelissier H. Chem. Rev. 2013; 113: 442

2 Taylor RJ. K, Reid M, Foot J, Raw SA. Acc. Chem. Res. 2005; 38: 851
3 Lena JI. C, Fernandez EM. S, Ramani A, Birlirakis N, Barrero AF, Arseniyadis S. Eur. J. Org. Chem. 2005; 683
4 Moody CL, Pugh DS, Taylor RJ. K. Tetrahedron Lett. 2011; 52: 2511

5a Reid M, Rowe DJ, Taylor RJ. K. Chem. Commun. 2003; 2284
5b MacCoss RN, Balskus EP, Ley SV. Tetrahedron Lett. 2003; 44: 7779

6 Oswald MF, Raw SA, Taylor RJ. K. Chem. Commun. 2005; 2253

7a Kadota S, Tezuka Y, Prasaim JK, Ali MS, Banskota AH. Curr. Top. Med. Chem. 2003; 3: 203
7b Claeson P, Claeson UP, Tuchinda P, Rentrakul V. Studies in Natural Product Chemistry . Vol. 26. Atta-ur Rahman. Elsevier; Amsterdam: 2002: 881

8 Yin J, Kouda K, Tezuka Y, Le Tran Q, Miyahara T, Chen Y, Kadota S. Planta Med. 2004; 70: 54
9 Hiebel MA, Pelotier B, Piva O. Tetrahedron 2007; 63: 7874
10 Yao H, Ren J, Tong R. Chem. Commun. 2013; 49: 193

11a Araujo CA. C, Alegrio LV, Leon LL. Phytochemistry 1998; 49: 751
11b Lee C-HA, Loh T.-P. Tetrahedron Lett. 2006; 47: 1641
11c Rogano F, Rüedi P. Helv. Chim. Acta 2010; 93: 1281

12a Tezuka Y, Ali MS, Banskota AH, Kadota S. Tetrahedron Lett. 2000; 41: 5903
12b Ko HM, Lee DG, Kim MA, Kim HJ, Park J, Lah MS, Lee E. Tetrahedron 2007; 63: 5797
12c Bunt AJ, Bailey CD, Cons BD, Edwards SJ, Elsworth JD, Pheko T, Willis CL. Angew. Chem. Int. Ed. 2012; 51: 3901

13 Nising FC, Bräse S. Chem. Soc. Rev. 2012; 41: 988

14a Bhattacharjee A, Soltani O, De Brabander JK. Org. Lett. 2002; 4: 481
14b Fuwa H, Noto K, Sasaki M. Org. Lett. 2010; 12: 1636
14c Wang L, Li P, Menche D. Angew. Chem. Int. Ed. 2010; 49: 9270
14d Asano K, Matsubara S. J. Am. Chem. Soc. 2011; 133: 16711
14e Cochet T, Roche D, Bellosta V, Cossy J. Eur. J. Org. Chem. 2012; 801
14f Krishna PR, Nomula R, Ramana DV. Tetrahedron Lett. 2012; 53: 3612

15a Olier C, Kaafarani M, Gastaldi S, Bertrand MP. Tetrahedron 2010; 66: 413
15b Pastor IM, Yus M. Curr. Org. Chem. 2012; 16: 1277
15c Han X, Peh G.-R, Floreancig PE. Eur. J. Org. Chem. 2013; 1193

16a Mahmood A, Suarez JR, Thomas SP, Aggarwal VK. Tetrahedron Lett. 2013; 54: 49
16b Raffier L, Izquierdo F, Piva O. Synthesis 2011; 4037
16c Saikia AK, Bondalapati S, Indukuri K, Gogoi P. Chem. Lett. 2011; 40: 1176

17a Miranda PO, Diaz DD, Padron JI, Bermejo J, Martin VS. Org. Lett. 2003; 5: 1979
17b Miranda PO, Carballo RM, Martin VS, Padron JI. Org. Lett. 2009; 11: 357
17c Zheng K, Liu X, Qin S, Xie M, Lin L, Hu C, Feng X. J. Am. Chem. Soc. 2012; 134: 17564

18 Clarisse D, Pelotier B, Piva O, Fache F. Chem. Commun. 2012; 48: 157
19 Clarisse D, Pelotier B, Fache F. Chem. Eur. J. 2013; 19: 857
20 Haines AH. Method of Oxidation of Organic Compounds . Academic Press; London: 1988

21a Indukuri K, Bondalapati S, Kotipalli T, Gogoi P, Saikia AK. Synlett 2012; 233
21b Reddy BV. S, Chaya DN, Yadav JS, Chatterjee D, Kunwar AC. Tetrahedron Lett. 2011; 52: 2961
21c Chio FK, Warne J, Gough D, Penny M, Green S, Coles SJ, Hursthouse MB, Jones P, Hassall L, McGuire TM, Dobbs AP. Tetrahedron 2011; 67: 5107
21d Reddy BV. S, Venkateswarlu A, Kumar CG. K. S. N, Vinu A. Tetrahedron Lett. 2010; 51: 6511
21e Yadav JS, Rajasekhar K, Murty MS. R. Tetrahedron Lett. 2005; 46: 2311

22a Knölker HJ. J. Prakt Chem. 1995; 337: 75
22b Reid M, Rowe DJ, Taylor RJ. K. Chem. Commun. 2003; 2284

23 Zhang W, Cue Jr. BW In Green Techniques for Organic Synthesis and Medicinal Chemistry. Wiley; Chichester: 2012

24a Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
24b Plietker B In Iron Catalysis in Organic Chemistry . Plietker B. Wiley-VCH; Weinheim: 2008
24c Sun C.-L, Li B.-J, Shi Z.-J. Chem. Rev. 2010; 110: 1293
24d Bézier D, Sortais J.-B, Darcel C. Adv. Synth. Catal. 2013; 355: 19

25a Cornelis A, Laszlo P. Synthesis 1980; 849
25b Cornelis A, Laszlo P. Synthesis 1985; 909
25c Delaude L, Laszlo P. J. Org. Chem. 1996; 61: 6360
25d Cseri T, Bekassy S, Figueras F. Bull. Soc. Chim. Fr. 1996; 133: 547
25e Varam RS, Dahiya R. Tetrahedron Lett. 1997; 38: 2043

26 As mentioned in ref. 25a, a gentle heating was required to induce the oxidation step in a reasonable time.
27 Whereas these procedures worked out very safely in our hands, nitrates are potentially hazardous compounds, and appropriate caution has to be applied for both steps. In particular, we urge to avoid confined conditions, and we recommend that appropriate safety tests be carried out before scale-up.

28a Baishya G, Sarmah B, Hazarika N. Synlett 2013; 24: 1137
28b Dintzner MR. Synlett 2013; 24: 1091

29 Typical ProcedureFor stability reasons, the catalyst was prepared just before use: Fe(NO₃)₃·9H₂O (112.5 mg, 0.27 mmol) was diluted in acetone (2 mL), and the resulting mixture was stirred for 5 min. Then, bentonite K10 (150 mg) was added, and the mixture was stirred for additional 5 min. After careful concentration until dryness, under vacuum at 50 °C (and strictly not at higher temperature), the resulting powder was immediately implicated in the oxidation procedure. Benzyl alcohol (0.5 mmol) in CH₂Cl₂ (1.5 mL) was added to the just prepared catalyst, and the resulting heterogeneous mixture was stirred at 35 °C until complete conversion (around 4 h, TLC monitoring). After cooling to r.t., homoallylic alcohol 3 (0.5 mmol) and trimethylsilylchloride (80 μL, 0.6 mmol) were added at once, and the reaction mixture was stirred for two additional hours at r.t. The crude mixture was then directly chromatographied to deliver the expected tetrahydropyran. All data were in agreement with the literature.
30 Alder RW, Harvey JN, Oakley MT. J. Am. Chem. Soc. 2002; 124: 4960
31 Carballo RM. Ramirez M. A, Rodriguez ML, Martin VS, Padron JI. Org. Lett. 2006; 8: 3837

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Supporting Information

Sequential Oxidation–Prins Reaction Processes Induced by the Same Iron Salt: Direct Access to 2-Aryl-4-Chloro-Tetrahydropyrans from Benzyl ­Alcohols

Sequential Oxidation–Prins Reaction Processes Induced by the Same Iron Salt: Direct Access to 2-Aryl-4-Chloro-Tetrahydropyrans from Benzyl Alcohols