Regio- and Stereoselective
Au(I)-Catalyzed Intermolecular Hydroalkoxylation of Aryl Allenes

Dong-Mei Cui; Ke-Rui Yu; Chen Zhang

doi:10.1055/s-0028-1088158

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2009(7): 1103-1106
DOI: 10.1055/s-0028-1088158

LETTER

Regio- and Stereoselective Au(I)-Catalyzed Intermolecular Hydroalkoxylation of Aryl Allenes

Dong-Mei Cui*^a, Ke-Rui Yu^a, Chen Zhang*^b
^a College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Fax: +86(571)88208459; e-Mail: cuidongmei@zjut.edu.cn;
^b School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China

Further Information

Publication History

Received 27 October 2008
Publication Date:
20 March 2009 (online)

Abstract
Full Text
References
Supplementary Material

Permissions and Reprints All articles of this category

Abstract

In the presence of a catalytic amount of Ph₃PAuNO₃ and H₂SO₄, the hydroalkoxylation of allenes with alcohols has been shown to proceed smoothly and give allylic ethers in good yields and high regio- and stereoselectivity.

Key words

allenes - catalysis - alcohols - regioselectivity - stereoselectivity - hydroalkoxylation

Supporting Information

References and Notes

Recent reviews, see:
1a Skouta R. Li C.-J. Tetrahedron 2008, 64: 4917

Search in Google Scholar
1b Shen HC. Tetrahedron 2008, 64: 3885

Search in Google Scholar
1c Muzart J. Tetrahedron 2008, 64: 3815

Search in Google Scholar
1d Hashmi ASK. Chem. Rev. 2007, 107: 3180

Search in Google Scholar
1e Hashmi ASK. Gold Bull. 2004, 37: 51

Search in Google Scholar
1f Arcadi A. Di Giuseppe S. Curr. Org. Chem. 2004, 8: 795

Search in Google Scholar
For examples, see:
2a Skouta R. Li CJ. Angew. Chem. Int. Ed. 2007, 46: 1117

Search in Google Scholar
2b Dube P. Toste FD. J. Am. Chem. Soc. 2006, 128: 12062

Search in Google Scholar
2c Casado R. Contel M. Laguna M. Romero P. Sanz S. J. Am. Chem. Soc. 2003, 125: 11925

Search in Google Scholar
2d Gonzalez-Arellano C. Abad A. Corma A. Garcia H. Iglesias M. Sanchez F. Angew. Chem. Int. Ed. 2007, 46: 1536

Search in Google Scholar
2e Zhang ZB. Widenhoefer RA. Angew. Chem. Int. Ed. 2007, 46: 283

Search in Google Scholar
2f Hashmi ASK. Weyrauch JP. Kurpejovi E. Frost TM. Miehlich B. Frey W. Bats JW. Chem. Eur. J. 2006, 12: 5806

Search in Google Scholar
2g LaLonde RL. Sherry BD. Kang EJ. Toste FD. J. Am. Chem. Soc. 2006, 129: 2452

Search in Google Scholar
2h Mézailles N. Ricard L. Gagosz F. Org. Lett. 2005, 7: 4133

Search in Google Scholar
2i Mézailles N. Ricard L. Gagosz F. Org. Lett. 2005, 7: 4133

Search in Google Scholar
3a Genin E. Toullec PY. Antoniotti S. Brancour C. Genêt J.-P. Michelet V. J. Am. Chem. Soc. 2006, 128: 3112

Search in Google Scholar
3b Sun J. Conley MP. Zhang L. Kozmin SA. J. Am. Chem. Soc. 2006, 128: 9705

Search in Google Scholar
3c Sherry BD. Maus L. Laforteza BN. Toste FD. J. Am. Chem. Soc. 2006, 128: 8132

Search in Google Scholar
3d Fukuda Y. Utimoto K. J. Org. Chem. 1991, 56: 3729

Search in Google Scholar
3e Fukuda Y. Utimoto K. Bull. Chem. Soc. Jpn. 1991, 64: 203

Search in Google Scholar
3f Mizushima E. Sato K. Hayashi T. Tanaka M. Angew. Chem. Int. Ed. 2002, 41: 4563

Search in Google Scholar
3g Roembke P. Schmidbaur H. Cronje S. Raubenheimer H. J. Mol. Catal. A: Chem. 2004, 212: 35

Search in Google Scholar
3h Mizushima E. Cui D.-M. Nath DCD. Hayashi T. Tanaka M. Org. Synth. 2006, 83: 55

Search in Google Scholar
3i Mizushima E. Sato K. Hayashi T. Tanaka M. Org. Lett. 2003, 5: 3349

Search in Google Scholar
4a Olsson L.-I. Claesson A. Synthesis 1979, 743
4b Marshall JA. Wolf MA. Wallace EM. J. Org. Chem. 1997, 62: 367

Search in Google Scholar
4c Deutsch C. Gockel B. Hoffmann-Röder A. Krause N. Synlett 2007, 1790
4d Hamilton GL. Kang EJ. Mba M. Toste FD. Science 2007, 317: 496

Search in Google Scholar
4e Volz F. Krause N. Org. Biomol. Chem. 2007, 5: 1519

Search in Google Scholar
4f Hashmi ASK. Blanco MC. Fischer D. Bats JW. Eur. J. Org. Chem. 2006, 1387
4g Erdsak J. Krause N. Synthesis 2007, 3741
4h Alcaide B. Almendros P. Martinez del Campo T. Angew. Chem. Int. Ed. 2007, 46: 6684

Search in Google Scholar
4i Zhang Z. Liu C. Kinder RE. Han X. Qian H. Widenhoefer RA. J. Am. Chem. Soc. 2006, 128: 9066

Search in Google Scholar
4j Zhang Z. Widenhoefer RA. Angew. Chem. Ind. Ed. 2007, 46: 283

Search in Google Scholar
4k Hoffmann-Röder A. Krause N. Org. Lett. 2001, 3: 2537

Search in Google Scholar
4l Gockel B. Krause N. Org. Lett. 2006, 8: 4485

Search in Google Scholar
4m Walkup RD. Park G. Tetrahedron Lett. 1987, 28: 1023

Search in Google Scholar
4n Ma S. Yu Z. Wu S. Tetrahedron 2001, 57: 1585

Search in Google Scholar
4o Yu X. Seo S.-Y. Marks TJ. J. Am. Chem. Soc. 2007, 129: 7244

Search in Google Scholar
5a Fukuda Y. Utimoto K. J. Org. Chem. 1991, 56: 3729

Search in Google Scholar
5b Fukuda Y, and Utimoto K. inventors; JP 04095039. ; Chem. Abstr. 1992, 117, 191330
6 Zhang Z. Widenhoefer RA. Org. Lett. 2008, 10: 2079

Crossref Search in Google Scholar
7 Nishina N. Yamamoto Y. Tetrahedron Lett. 2008, 49: 1023

Search in Google Scholar
8a Zhang C. Cui D.-M. Yao L.-Y. Wang B.-S. Hu Y.-Z. Hayashi T. J. Org. Chem. 2008, 73: 7811

Search in Google Scholar
8b Cui D.-M. Zheng Z.-L. Zhang C. J. Org. Chem. 2009, 74: 1426

Search in Google Scholar
8c Cui D.-M. Meng Q. Zheng J.-Z. Zhang C. Chem. Commun. 2009, DOI: 10.1039/b818863g

9

Typical Experimental Procedure
To a reactor containing allene (0.5 mmol), Ph_3PAuNO₃ (0.01 mmol), and alcohol (0.6 mmol) was added H₂SO₄ (0.025 mmol). The mixture was then sealed and stirred at 40 ˚C for 4 h. It was quenched with sat. soln of NaHCO₃ and then extracted with EtOAc (3 × 10 mL). The organic layer was washed with brine, dried over Na₂SO₄, and concentrated in vacuo. The residue was purified by flash chromatography to give the pure product.
( E )-1-Butyl-4-(3-methoxyprop-1-enyl)benzene (3i)
^¹H NMR (500 MHz, CDCl₃): δ = 7.30 (d, J = 8.5 Hz, 2 H), 7.12 (d, J = 8.5 Hz, 2 H), 6.57 (d, J = 16.0 Hz, 1 H), 6.23 (dt, J = 16.0, 6.0 Hz, 1 H), 4.07 (dd, J = 6.0, 1.5 Hz, 2 H), 3.37 (s, 3 H), 2.58 (t, J = 7.5 Hz, 2 H), 1.60-1.56 (m, 2 H), 1.37-1.32 (m, 2 H), 0.92 (t, J = 7.5 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.6, 134.1, 132.5, 128.6, 126.4, 124.9, 73.2, 57.9, 35.4, 33.5, 22.3, 13.9. IR: ν = 2950, 2929, 2958, 1635, 1512, 1456, 1384, 1191, 1119, 968, 847, 553 cm^-¹. HRMS: m/z calcd for C₁₄H₂₀O [M + 1⁺]; 205.1592; found: 205.1591.
( E )-1-Butyl-4-(3-ethoxyprop-1-enyl)benzene (3j)
^¹H NMR (500 MHz, CDCl₃): δ = 7.80 (d, J = 8.0 Hz, 2 H), 7.12 (d, J = 8.0 Hz, 2 H), 6.57 (d, J = 16.0 Hz, 1 H), 6.26 (dt, J = 16.0, 6.0 Hz, 1 H), 4.12 (dd, J = 6.0, 1.5 Hz, 2 H), 3.54 (q, J = 7.0 Hz, 2 H), 2.59 (t, J = 7.5 Hz, 2 H), 1.60-1.55 (m, 2 H), 1.39-1.30 (m, 2 H), 1.24 (t, J = 7.0 Hz, 3 H), 0.92 (t, J = 7.5 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.5, 134.2, 132.3, 128.6, 126.4, 125.3, 71.4, 65.6, 35.4, 33.6, 22.4, 15.3, 14.0. IR: ν = 2928, 1636, 1508, 1384, 1095, 526 cm^-¹. HRMS: m/z calcd for C₁₅H₂₂O [M⁺]: 218.1671; found: 218.1680. ( E )-1-Butyl-4-(3-isopropoxyprop-1-enyl)benzene (3k)
^¹H NMR (500 MHz, CDCl₃): δ = 7.29 (d, J = 8.0 Hz, 2 H), 7.11 (d, J = 8.0 Hz, 2 H), 6.55 (d, J = 16.0 Hz, 1 H), 6.26 (dt, J = 16.0, 6.5 Hz, 1 H), 4.12 (dd, J = 6.5, 1.5 Hz, 2 H), 3.71-3.63 (m, 1 H), 2.58 (t, J = 7.5 Hz, 2 H), 1.63-1.55 (m, 2 H), 1.37-1.30 (m, 2 H), 1.20 (d, J = 6.0 Hz, 6 H), 0.92 (t, J = 7.5 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.5, 134.4, 131.9, 128.7, 126.5, 126.0, 70.9, 69.0, 35.5, 33.7, 22.5, 22.3, 14.1. IR: ν = 2932, 1614, 1558, 1515, 1456, 1384, 1247, 1156, 1137, 1029, 810, 749, 551 cm^-¹. HRMS: m/z calcd for C₁₆H₂₄O [M⁺]: 232.1827; found: 232.1830. ( E )-1-(3- tert -Butoxyprop-1-enyl)-4-butylbenzene (3l)
^¹H NMR (500 MHz, CDCl₃): δ = 7.29 (d, J = 8.0 Hz, 2 H), 7.10 (d, J = 8.0 Hz, 2 H), 6.57 (d, J = 16.0 Hz, 1 H), 6.25 (dt, J = 16.0, 6.0 Hz, 1 H), 4.06 (dd, J = 6.0, 1.5 Hz, 2 H), 2.58 (t, J = 7.5 Hz, 2 H), 1.61-1.54 (m, 2 H), 1.36-1.31 (m, 2 H), 1.25 (s, 9 H), 0.92 (t, J = 7.5 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.2, 134.5, 131.2, 128.5, 126.6, 126.3, 73.3, 63.0, 35.4, 33.6, 27.7, 22.4, 14.0. IR: ν = 2958, 2929, 2858, 1681, 1625, 1512, 1457, 1384, 1194, 1122, 969, 525 cm^-¹. HRMS: m/z calcd for C₁₇H₂₆O [M⁺]: 246.1984; found: 246.1989.
( E )-1-(3-Methoxyprop-1-enyl)-4-pentylbenzene (3m)
^¹H NMR (500 MHz, CDCl₃): δ = 7.30 (d, J = 8.5 Hz, 2 H), 7.12 (d, J = 8.5 Hz, 2 H), 6.57 (d, J = 16.0 Hz, 1 H), 6.23 (dt, J = 16.0, 6.0 Hz, 1 H), 4.06 (dd, J = 6.0, 1.5 Hz, 2 H), 3.37 (s, 3 H), 2.57 (t, J = 7.5 Hz, 2 H), 1.63-1.56 (m, 2 H), 1.34-1.29 (m, 4 H), 0.88 (t, J = 7.0 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.6, 134.1, 132.5, 128.6, 126.4, 124.9, 73.2, 57.8, 35.6, 31.5, 31.1, 22.5, 14.0. IR: ν = 2927,2855, 1634, 1384, 1124, 544 cm^-¹. HRMS: m/z calcd for C₁₅H₂₂O [M⁺]: 218.1671; found: 218.1665.
( E )-1-(3-Ethoxyprop-1-enyl)-4-pentylbenzene (3n)
^¹H NMR (500 MHz, CDCl₃): δ = 7.29 (d, J = 8.0 Hz, 2 H), 7.10 (d, J = 8.0 Hz, 2 H), 6.57 (d, J = 16.0 Hz, 1 H), 6.25 (dt, J = 16.0, 6.0 Hz, 1 H), 4.11 (dd, J = 6.0, 1.5 Hz, 2 H), 3.53 (q, J = 7.0 Hz, 2 H), 2.57 (t, J = 7.5 Hz, 2 H), 1.63-1.56 (m, 2 H), 1.33-1.30 (m, 4 H), 1.24 (t, J = 7.0 Hz, 3 H), 0.88 (t, J = 7.0 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.5, 134.2, 132.2, 128.6, 126.4, 125.3, 71.3, 65.6, 35.6, 31.5, 31.1, 22.5, 15.2, 14.0. IR: ν = 2950, 2927, 2855, 1652, 1558, 1506, 1456, 1384, 1100, 968, 539 cm^-¹. HRMS: m/z calcd for C₁₆H₂₄O [M⁺]: 232.1831; found: 232.1827.

( E )-1-(3-Isopropoxyprop-1-enyl)-4-pentylbenzene (3o)
^¹H NMR (500 MHz, CDCl₃): δ = 7.29 (d, J = 8.0 Hz, 2 H), 7.11 (d, J = 8.0 Hz, 2 H), 6.57 (d, J = 15.5 Hz, 1 H), 6.25 (dt, J = 15.5, 6.0 Hz, 1 H), 4.12 (dd, J = 6.0, 1.5 Hz, 2 H), 3.71-3.65 (m, 1 H), 2.57 (t, J = 7.5 Hz, 2 H), 1.63-1.56 (m, 2 H), 1.34-1.29 (m, 4 H), 1.20 (d, J = 6.0 Hz, 6 H), 0.88 (t, J = 7.0 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 142.4, 134.3, 131.8, 128.5, 126.4, 125.8, 70.8, 68.8, 35.6, 31.5, 31.1, 22.5, 22.1, 14.0. IR: ν = 2950, 2927, 2856, 1633, 1384, 1123, 1070, 965, 544 cm^-¹. HRMS: m/z calcd for C₁₇H₂₆O [M⁺]: 246.1984; found: 246.1981.
( E )-1-(3-Isopropoxyprop-1-enyl)-4-methoxybenzene (3r)
^¹H NMR (500 MHz, CDCl₃): δ = 7.33-7.31 (m, 2 H), 6.85-6.83 (m, 2 H), 6.54 (d, J = 15.5 Hz, 1 H), 6.17 (dt, J = 15.5, 6.0 Hz,1 H), 4.11 (dd, J = 6.0, 1.5 Hz, 2 H), 3.80 (s, 3 H), 3.71-3.65 (m, 1 H), 1.20 (d, J = 6.0 Hz, 6 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 159.2, 131.5, 129.7, 127.6, 124.6, 113.9, 70.8, 68.9, 55.3, 22.2. IR: ν = 2872, 1634, 1558, 1491, 1407, 1384, 1088, 1038, 1013, 937, 804, 485 cm^-¹. HRMS: m/z calcd for C₁₃H₁₈O [M + 1⁺]: 207.1385; found: 207.1385.

( E )-1-(3-Ethoxyprop-1-enyl)-3-fluorobenzene (3u)
^¹H NMR (500 MHz, CDCl₃₎: δ = 7.28-7.24 (m, 1 H), 7.15-7.13 (m, 1 H), 7.10-7.06 (m, 1 H), 6.94-6.90 (m, 1 H), 6.58 (d, J = 16.0 Hz, 1 H), 6.30 (dt, J = 16.0, 6.0 Hz, 1 H), 4.14 (dd, J = 6.0, 1.5 Hz, 2 H), 3.56 (q, J = 7.0 Hz, 2 H), 1.25 (t, J = 7.0 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 163.1 (d, J = 243.8 Hz), 139.2 (d, J = 8.8 Hz), 130.8, 129.9 (d, J = 8.8 Hz), 127.8, 122.3, 114.3 (d, J = 21.3 Hz), 112.9 (d, J = 21.3 Hz), 70.9, 65.9, 15.2. IR: ν = 2995, 1770, 1759, 1635, 1834, 1246, 1058, 913, 743, 526 cm^-¹. HRMS: m/z calcd for C₁₁H₁₃FO [M⁺]: 180.0950; found: 180.0946. ( E )-1-Bromo-3,4-dimethoxy-2-(3-methoxybut-1-enyl)-benzene (3v) ^¹H NMR (500MHz, CDCl₃): δ = 7.29 (d, J = 8.5 Hz, 2 H), 6.70 (d, J = 8.5 Hz, 2 H), 6.48 (d, J = 16.0 Hz, 1 H), 6.14 (dd, J = 16.0, 7.5 Hz, 1 H), 3.95-3.90 (m, 1 H), 3.86 (s, 3 H), 3.75 (s, 3 H), 3.38 (s, 3 H), 1.36 (dd, J = 6.5, 2.5 Hz, 3 H). ^¹³C NMR (125 MHz, CDCl₃): δ = 152.6, 148.1, 138.8, 131.2, 128.1, 125.9, 114.6, 112.1, 78.7, 60.1, 56.2, 56.0, 21.6. IR: ν = 2928, 1636, 1508, 1384, 1095, 526 cm^-¹. HRMS: m/z calcd for C₁₃H₁₇BrO₃ [M⁺]: 300.0361; found: 300.0341.

Supplementary Material

Supporting Information