One-Pot Access to Cinnamates via Direct Oxidative C–H Transformation of Allylarenes

Meng-Yang Chang; Shin-Ying Lin; Chieh-Kai Chan

doi:10.1055/s-0032-1318146

Synlett, Table of Contents

Synlett 2013; 24(4): 487-490
DOI: 10.1055/s-0032-1318146

letter

One-Pot Access to Cinnamates via Direct Oxidative C–H Transformation of Allylarenes

Meng-Yang Chang*

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Fax: +886(7)3125339 Email: mychang@kmu.edu.tw

,

Shin-Ying Lin

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Fax: +886(7)3125339 Email: mychang@kmu.edu.tw

,

Chieh-Kai Chan

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan Fax: +886(7)3125339 Email: mychang@kmu.edu.tw

› Author Affiliations

Abstract

All articles of this category

Abstract

A highly selective combination of ruthenium complex and oxidant, which catalyzes the oxidative C–H esterification of allylarenes to the corresponding bis-(E)-cinnamates and (E)-cinnamates, is described. The one-pot route was carried out by olefinic migration of allylarenes with RuCl₂(PPh₃)₃ and DDQ-mediated allylic oxidation of the resulting internal alkenes with various alcohols in good yields.

Key words

allylarenes - C–H esterification - cinnamates

Full Text

References

References and Notes

For reviews, see:

1a Godula K, Sames D. Science 2006; 312: 67
1b Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
1c Campos KR. Chem. Soc. Rev. 2007; 36: 1069
1d Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
1e Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
1f Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
1g Chen MS, White MC. Science 2007; 318: 783

2 Chen H, Jiang H, Cai C, Dong J, Fu W. Org. Lett. 2011; 13: 992

3a Muzart J. Tetrahedron Lett. 1987; 28: 4665
3b Uemura S, Patil SR. Tetrahedron Lett. 1982; 23: 4353

4a Reed SA, White MC. J. Am. Chem. Soc. 2008; 130: 3316
4b Rice GT, White MC. J. Am. Chem. Soc. 2009; 131: 11707
4c Fraunhoffer KJ, White MC. J. Am. Chem. Soc. 2007; 129: 7274
4d Shimizu Y, Obora Y, Ishii Y. Org. Lett. 2010; 12: 1372
4e Liu G, Yin G, Wu L. Angew. Chem. Int. Ed. 2008; 47: 4733

5 Qin C, Jiao N. J. Am. Chem. Soc. 2010; 132: 15893

6a Young AJ, White MC. J. Am. Chem. Soc. 2008; 130: 14090
6b Lin S, Song CX, Cai GX, Wang WH, Shi ZJ. J. Am. Chem. Soc. 2008; 130: 12901

7 Chen MS, White MC. J. Am. Chem. Soc. 2004; 126: 1346
8 Delcamp JH, White MC. J. Am. Chem. Soc. 2006; 128: 15076

9a Chang M.-Y, Lee T.-W, Lin S.-Y. Tetrahedron 2013; 69: 228
9b Chang M.-Y, Lee T.-W, Wu M.-H. Heterocycles 2012; 85: 1607
9c Chang M.-Y, Lee T.-W, Wu M.-H. Org. Lett. 2012; 14: 2198

For DDQ-mediated reactions, see:

10a Akhlaghinia B, Pourali AR. Synthesis 2004; 1747
10b Rahim MA, Matsumura S, Toshima K. Tetrahedron Lett. 2005; 46: 7307
10c Zhou W, Xu J, Zhang L, Jiao N. Org. Lett. 2010; 12: 2888
10d Liu W, Jiang H, Zhang M, Qi C. J. Org. Chem. 2010; 75: 966
10e Bose DS, Idrees M, Srikanth B. Synthesis 2007; 819
10f Hilt G, Danz M. Synthesis 2008; 2257
10g Hilt G, Smolko KI. Angew. Chem. Int. Ed. 2003; 42: 2795
10h Manning JR, Davies HM. L. J. Am. Chem. Soc. 2008; 130: 8602
10i Sharma A, Sharma N, Shard A, Kumar R, Mohanakrishnan D, Sinha AK, Sahal D. Org. Biomol. Chem. 2011; 9: 5211
10j Iliefski T, Li S, Lundquist K. Tetrahedron Lett. 1998; 39: 2413

11 CCDC 896676 (5) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].

12a Kuznik N, Krompiec S, Bieg T, Baj S, Skutil K, Chrobok A. J. Organomet. Chem. 2003; 665: 167
12b Krompiec S, Pigulla M, Krompiec M, Baj S, Mrowiec-Białon J, Kasperczyk J. Tetrahedron Lett. 2004; 45: 5257
12c Zoran A, Sasson Y. J. Org. Chem. 1981; 46: 255
12d Wang M, Yang X.-F, Li CJ. Eur. J. Org. Chem. 2003; 998
12e Wang M, Li C.-J. Tetrahedron Lett. 2002; 43: 3589

13 Representative Synthetic Procedure of Skeletons 3, 8, and 10 RuCl₂(PPh₃)₃ (38 mg, 0.04 mmol) was added to a solution of skeleton 2, 7, or 9 (0.4 mmol) in CH₂Cl₂ (10 mL) at reflux for 2 h. The reaction mixture was cooled to r.t. Then alcohols (1 mL) and DDQ (for skeleton 2: 900 mg, 4.0 mmol; for skeleton 7 or 9: 450 mg, 2.0 mmol) were added to the reaction mixture. The reaction mixture was stirred at reflux for 1 h. The reaction mixture was cooled to r.t. The residue was diluted with H₂O (10 mL), and the mixture was extracted with CH₂Cl₂ (3 × 20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product. Purification on silica gel (hexanes–EtOAc = 10:1 to 6:1) afforded skeletons 3, 8, and 10.

14a Padwa A, Sa MM. Tetrahedron Lett. 1997; 38: 5087
14b Gagneux A, Winstein S, Young WG. J. Am. Chem. Soc. 1960; 82: 5956

15a Joshi BP, Sharma A, Sinha AK. Tetrahedron 2006; 62: 2590
15b Iranpoor N, Firouzabadi H, Nowrouzi N, Khalili D. Tetrahedron 2009; 65: 3893
15c Sinha AK, Sharma A, Swaroop A, Kumar V. Tetrahedron 2007; 63: 1000
15d Cosner CC, Cabrera PJ, Byrd KM, Thomas AM. A, Helquist P. Org. Lett. 2011; 13: 2071

16a Cheng D, Bao W. Adv. Synth. Catal. 2008; 350: 1263
16b Li Y.-Z, Li B.-J, Lu X.-Y, Lin S, Shi Z.-J. Angew. Chem. Int. Ed. 2009; 48: 3817
16c Zhang Y, Li C.-J. J. Am. Chem. Soc. 2009; 48: 3817
16d Liu L, Floreancig PE. Org. Lett. 2009; 11: 3152
16e Mo H, Bao W. Tetrahedron 2011; 67: 4793
16f Joshi BP, Sharma A, Sinha AK. Tetrahedron 2005; 61: 3075
16g Liu L, Floreancig PE. Org. Lett. 2010; 12: 4686