Efficient One-Pot Synthesis of 2-Aryldihydrobenzofuran

Chongfeng Pan; Zhixiong Ma; Jie Yu; Zuhui Zhang; Ailing Hui; Zhiyong Wang

doi:10.1055/s-2005-871940

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 2005(12): 1922-1926
DOI: 10.1055/s-2005-871940

LETTER

Efficient One-Pot Synthesis of 2-Aryldihydrobenzofuran

Chongfeng Pan, Zhixiong Ma, Jie Yu, Zuhui Zhang, Ailing Hui, Zhiyong Wang*
Hefei National Laboratory for Physical Science at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China
Fax: +86(551)3603185; e-Mail: zwang3@ustc.edu.cn;

Further Information

Publication History

Received 9 May 2005
Publication Date:
07 July 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A series of 2-aryldihydrobenzofuran derivatives were successfully synthesized from the corresponding carbonyl compounds and (2-bromobenzyl)trimethylsilane by the one-pot benzylation-substitution procedure.

Key words

one-pot synthesis - 2-aryldihydrobenzofuran - benzylation - intramolecular Ullmann coupling - chemoselectivity

References

1a Ward RS. Nat. Prod. Rep. 1993, 10: 1

Crossref PubMed Google Scholar
1b Ward RS. Nat. Prod. Rep. 1995, 12: 183

Crossref PubMed Google Scholar
1c Ward RS. Nat. Prod. Rep. 1997, 14: 43

Crossref PubMed Google Scholar
1d Valcic S. Montenegro G. Timmermann BN. J. Nat. Prod. 1998, 61: 771

Crossref PubMed Google Scholar
1e Cho JY. Baik KU. Yoo ES. Yoshikawa K. Park MH. J. Nat. Prod. 2000, 63: 1205

Crossref PubMed Google Scholar
1f Li SY. Fuchino H. Kawahara N. Sekita S. Satake M. J. Nat. Prod. 2002, 65: 262

Crossref PubMed Google Scholar
1g Beldjoudi N. Mambu L. Labaied M. Grellier P. Ramanitrahasimbola D. Rasoanaivo P. Martin MT. Frappier F. J. Nat. Prod. 2003, 66: 1447

Crossref PubMed Google Scholar
2 Akai S. Morita N. Iio K. Nakamura Y. Kita Y. Org. Lett. 2000, 2: 2279 ; and references cited therein

Crossref Google Scholar
3a Engler TA. Combrink KD. Ray JE. J. Am. Chem. Soc. 1988, 110: 7931

Crossref Google Scholar
3b Wang S. Gates BD. Swenton JS. J. Org. Chem. 1991, 56: 1979

Crossref Google Scholar
3c Gates BD. Dalidowicz P. Tebben A. Wang S. Swenton JS. J. Org. Chem. 1992, 57: 2135

Crossref Google Scholar
3d Engler TA. Combrink KD. Lynch KO. Ray JE. J. Org. Chem. 1994, 59: 6567

Crossref Google Scholar
3e Engler TA. Wei D. Letavic MA. Combrink KD. Reddy JP. J. Org. Chem. 1994, 59: 6588

Crossref Google Scholar
3f Engler TA. Gfesser GA. Draney BW. J. Org. Chem. 1995, 60: 3700

Crossref Google Scholar
3g Engler TA. Chai W. Kenneth OL. J. Org. Chem. 1996, 61: 9297

Crossref Google Scholar
3h Snider BB. Han L. Xie C. J. Org. Chem. 1997, 62: 6978

Crossref Google Scholar
3i Engler TA. Letavic MA. Iyengar R. LaTessa KO. Reddy JP. J. Org. Chem. 1999, 64: 2391

Crossref Google Scholar
3j Chiba K. Fukuda M. Kim S. Kitano Y. Tada M. J. Org. Chem. 1999, 64: 7654

Crossref Google Scholar
3k Pieters L. Dyck SV. Gao M. Bai R. Hamel E. Vlietinck A. Lemiere G. J. Med. Chem. 1999, 42: 5475

Crossref Google Scholar
3l Itoh T. Kawai K. Hayase S. Ohara H. Tetrahedron Lett. 2003, 44: 4081

Crossref Google Scholar
4 Benbow JW. Katoch-Rouse R. J. Org. Chem. 2001, 66: 4965 ; and references cited therein

Crossref Google Scholar
For recent examples, see:
5a Zhu J. Price PA. Zhao SX. Skonezny PM. Tetrahedron Lett. 2000, 41: 4011

Crossref Google Scholar
5b Fagan PJ. Hauptman E. Shapiro R. Casalnuovo A. J. Am. Chem. Soc. 2000, 122: 5043

Crossref Google Scholar
5c Palucki M. Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1996, 118: 10333

Crossref Google Scholar
5d Torraca KE. Kuwabe S.-I. Buchwald SL. J. Am. Chem. Soc. 2000, 122: 12907

Crossref Google Scholar
6 Marcoux J.-F. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

Crossref Google Scholar
7 Bennetau B. Bordeau M. Dunogues J. Bull. Soc. Chim. Fr. 1981, 90

Google Scholar
8 Bartoli G. Basco M. Caretti D. Dalpozzo R. Todesco PE. J. Org. Chem. 1987, 52: 4381

Crossref Google Scholar
9 Gallagher MJ. Harvey S. Raston CL. Sue RE. J. Chem. Soc., Chem. Commun. 1988, 4: 289

Google Scholar
10 Cox DP. Terpinski J. Lawrynowicz W. J. Org. Chem. 1984, 49: 3216

Google Scholar
12 Hosomi A. Shirahata A. Sakurai H. Tetrahedron Lett. 1978, 19: 3043

Crossref Google Scholar

11

General Procedure for the One-Pot Synthesis of 2-Aryldihydrobenzofuran. Aldehyde (1 mmol) and BTMS (3 mmol) were dissolved in THF (4 mL), then 0.15 mL TBAF solution (1 M in THF) was added in one portion. The mixture was stirred at 35-40 °C for 30 min. After adding another 1 mmol of anhyd TBAF to the system, the solvent was evaporated under high vacuum. Then the residue was redissolved in 6 mL toluene. Under the nitrogen atmosphere, NaH (2 mmol) was added to the system with stirring. After stirring at 35-40 °C for 30 min, CuCl (5 mg) was added. The system was refluxed for 6-8 h, and then cooled to r.t. After being transferred to a 100 mL separatory funnel, the reaction mixture was diluted with 60 mL Et₂O. The organic layer was washed with 2 M HCl (5 mL), H₂O (10 mL) and brine (5 mL), then dried (anhyd MgSO₄). After evaporation of the solvent, the residue was purified by chromatography on silica gel to give the product. In the cases of 1g, 1j and 1k, the toluene was evaporated after the completion of the reaction and the mixture was directly purified by chromatography on silica gel.
Compound 1a: ¹H NMR (300 MHz, CDCl₃): δ = 7.34 (s, 4 H), 7.20-7.15 (m, 2 H), 6.92-6.86 (m, 2 H), 5.73 (dd, J = 8.1, 9.4 Hz, 1 H), 3.63 (dd, J = 9.4, 15.6 Hz, 1 H), 3.16 (dd, J = 8.1, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.50, 140.63, 133.79, 128.87, 128.40, 127.23, 126.20, 124.99, 120.94, 109.50, 83.28, 38.50. IR (film): ν = 3051, 2926, 1720, 1599, 1492, 1479, 1462, 1232 cm^-1. HRMS: m/z calcd for C₁₄H₁₁O³⁵Cl: 230.0499; found: 230.0490.
Compound 1b: ¹H NMR (300 MHz, CDCl₃): δ = 7.30 (d, J = 8.1 Hz, 2 H), 7.22-7.13 (m, 4 H), 6.90-6.84 (m, 2 H), 5.72 (dd, J = 8.9, 8.8 Hz, 1 H), 3.60 (dd, J = 8.9, 15.6 Hz, 1 H), 3.16 (dd, J = 8.8, 15.6 Hz, 1 H), 2.35 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.75, 139.02, 137.91, 129.41, 128.28, 126.75, 125.96, 124.95, 120.68, 109.47, 84.17, 38.46, 21.29. IR (film): ν = 3031, 2921, 1716, 1596, 1516, 1480, 1462, 1232 cm^-1. HRMS: m/z calcd for C₁₅H₁₄O: 210.1048; found: 210.1054.
Compound 1c: ¹H NMR (300 MHz, CDCl₃): δ = 7.34 (d, J = 8.8 Hz, 2 H), 7.20-7.13 (m, 2 H), 6.91-6.83 (m, 4 H), 5.70 (dd, J = 8.8, 8.9 Hz, 1 H), 3.81 (s, 3 H), 3.58 (dd, J = 8.9, 15.6 Hz, 1 H), 3.16 (dd, J = 8.8, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.67, 159.58, 133.97, 128.29, 127.46, 126.80, 124.93, 120.66, 114.11, 109.46, 84.10, 55.42, 38.43. IR (film): ν = 2914, 2843, 1613, 1516, 1460, 1301, 1248, 1029, 829 cm^-1. HRMS: m/z calcd for C₁₅H₁₄O₂: 226.0997; found: 226.1008.
Compound 1d: ¹H NMR (300 MHz, CDCl₃): δ = 7.43 (m, 1 H), 7.26 (m, 1 H), 7.16-7.14 (m, 2 H), 6.94-6.85 (m, 4 H), 6.04 (dd, J = 7.7, 9.5 Hz, 1 H), 3.86 (s, 3 H), 3.58 (dd, J = 9.5, 15.8 Hz, 1 H), 3.16 (dd, J = 7.7, 15.8 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.84, 156.06, 130.79, 128.69, 128.04, 127.00, 125.82, 125.05, 120.64, 120.62, 110.37, 109.40, 79.47, 55.46, 37.61. IR (film): ν = 3050, 2937, 2837, 1598, 1492, 1480, 1462, 1235 cm^-1. HRMS: m/z calcd for C₁₅H₁₄O₂: 226.0997; found: 226.0995.
Compound 1e: ¹H NMR (300 MHz, CDCl₃): δ = 7.20-7.16 (m, 2 H), 6.90-6.78 (m, 5 H), 5.95 (s, 2 H), 5.66 (dd, J = 8.7, 8.8 Hz, 1 H), 3.86 (s, 3 H), 3.58 (dd, J = 8.8, 15.7 Hz, 1 H), 3.19 (dd, J = 8.7, 15.7 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.55, 148.06, 147.53, 135.87, 128.31, 126.56, 124.92, 120.74, 119.65, 109.44, 108.26, 106.43, 101.20, 84.10, 38.42. IR (film): ν = 3032, 2897, 2778, 1597, 1504, 1480, 1461, 1444, 1232 cm^-1. HRMS: m/z calcd for C₁₅H₁₂O₃: 240.0789; found: 240.0782.
Compound 1f: ¹H NMR (300 MHz, CDCl₃): δ = 7.34 (dd, J = 1.9, 6.7 Hz, 2 H), 7.22-7.12 (m, 2 H), 7.03 (dd, J = 1.9, 6.7 Hz, 2 H), 6.91-6.83 (m, 2 H), 5.71 (dd, J = 8.8, 8.9 Hz, 1 H), 5.18 (s, 2 H), 3.59 (dd, J = 8.9, 15.6 Hz, 1 H), 3.47 (s, 3 H), 3.21 (dd, J = 8.8, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.60, 157.11, 135.21, 128.60, 127.33, 126.67, 124.87, 120.63, 116.80, 109.39, 94.39, 83.86, 55.99, 38.27. IR (film): ν = 2954, 2826, 1611, 1513, 1480, 1461, 1232, 1152, 1003 cm^-1. HRMS: m/z calcd for C₁₆H₁₆O₃: 256.1103; found: 256.1091.
Compound 1g: ¹H NMR (300 MHz, CDCl₃): δ = 7.29 (dd, J = 1.9, 8.7 Hz, 2 H), 7.20-7.12 (m, 2 H), 6.89-6.81 (m, 2 H), 6.73 (dd, J = 1.9, 8.7 Hz, 2 H), 5.67 (dd, J = 8.9, 8.9 Hz, 1 H), 3.54 (dd, J = 8.9, 15.7 Hz, 1 H), 3.26 (dd, J = 8.9, 15.7 Hz, 1 H), 2.95 (s, 6 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.76, 150.70, 129.15, 128.16, 127.37, 127.19, 124.84, 120.40, 112.59, 109.42, 84.67, 40.68, 38.00. IR (film): ν = 3030, 2888, 2803, 1615, 1524, 1479, 1460, 1353, 1232 cm^-1. HRMS: m/z calcd for C₁₆H₁₇NO: 239.1351; found: 239.1352.
Compound 1h: ¹H NMR (300 MHz, CDCl₃): δ = 7.92-6.91 (m, 11 H), 6.45 (dd, J = 1.9, 8.7 Hz, 2 H), 5.67 (dd, J = 8.1, 9.5 Hz, 1 H), 3.87 (dd, J = 9.5, 15.6 Hz, 1 H), 3.26 (dd, J = 8.1, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.78, 137.57, 134.07, 129.97, 129.18, 128.42, 126.53, 126.38, 125.82, 125.60, 125.25, 123.28, 122.78, 120.93, 109.71, 109.58, 81.96, 38.23. IR (film): ν = 3051, 2926, 1713, 1596, 1510, 1480, 1460, 1325, 1234 cm^-1. HRMS: m/z calcd for C₁₈H₁₄O: 246.1048; found: 246.1056.
Compound 1i: ¹H NMR (300 MHz, CDCl₃): δ = 7.43 (dd, J = 0.7, 1.8 Hz, 1 H), 7.26-7.12 (m, 2 H), 6.89-6.80 (m, 2 H), 6.42 (d, J = 3.3 Hz, 1 H), 6.37 (dd, J = 1.8, 3.3 Hz, 1 H), 5.74 (t, J = 8.9 Hz, 1 H), 3.50 (d, J = 8.9 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.00, 153.07, 143.23, 128.32, 126.29, 124.80, 120.80, 110.45, 109.65, 108.42, 77.02, 34.26. IR (film): ν = 3055, 2957, 2927, 1714, 1597, 1480, 1462, 1234 cm^-1. HRMS: m/z calcd for C₁₂H₁₀O₂: 186.0683; found: 186.0680.
Compound 1j: ¹H NMR (300 MHz, CDCl₃): δ = 8.61 (d, J = 5.9 Hz, 2 H), 7.36 (d, J = 5.9 Hz, 2 H), 7.22-7.17 (m, 2 H), 6.94-6.89 (m, 2 H), 5.77 (dd, J = 7.7, 9.8 Hz, 1 H), 3.73 (dd, J = 9.8, 15.5 Hz, 1 H), 3.15 (dd, J = 7.7, 15.5 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.31, 151.13, 150.12, 128.51, 125.51, 125.03, 121.21, 120.35, 109.55, 81.93, 38.11. IR (film): ν = 3031, 2918, 1597, 1561, 1480, 1462, 1412, 1233 cm^-1. HRMS: m/z calcd for: C₁₃H₁₁NO: 197.0880; found: 197.0884.
Compound 1k: ¹H NMR (300 MHz, CDCl₃): δ = 8.66 (s, 1 H), 8.58 (d, J = 3.7 Hz, 1 H), 7.75 (d, J = 7.9 Hz, 1 H), 7.31 (dd, J = 3.7, 7.9 Hz, 1 H), 7.22-7.16 (m, 2 H), 6.94-6.88 (m, 2 H), 5.79 (dd, J = 8.2, 9.1 Hz, 1 H), 3.69 (dd, J = 9.1, 15.6 Hz, 1 H), 3.15 (dd, J = 8.2, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 159.28, 149.40, 147.57, 137.55, 133.39, 128.51, 125.84, 124.97, 123.64, 121.08, 109.51, 81.56, 38.21. IR (film): ν = 3034, 2919, 1597, 1578, 1479, 1462, 1427, 1326, 1232 cm^-1. HRMS: m/z calcd for C₁₃H₁₁NO: 197.0880; found: 197.0873.
Compound 1l: ¹H NMR (300 MHz, CDCl₃): δ = 7.47 (m, 4 H), 7.33-7.15 (m, 8 H), 6.97-6.86 (m, 2 H), 3.92 (s, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 158.74, 145.49, 128.40, 138.37, 127.48, 126.37, 126.11, 124.84, 120.91, 109.69, 92.48, 44.46. IR (film): ν = 3057, 1596, 1480, 1461, 1447, 1240 cm^-1. HRMS: m/z calcd for C₂₀H₁₆O: 272.1205; found: 272.1212.
Compound 1m: ¹H NMR (300 MHz, CDCl₃): δ = 8.04 (d, J = 8.3 Hz, 2 H), 7.47 (d, J = 8.3 Hz, 2 H), 7.17 (m, 2 H), 6.90 (m, 2 H), 5.80 (dd, J = 8.0, 9.6 Hz, 1 H), 3.91 (s, 3 H), 3.68 (dd, J = 9.6, 15.6 Hz, 1 H), 3.17 (dd, J = 8.0, 15.6 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 166.83, 159.55, 147.27, 130.06, 129.79, 128.43, 126.05, 125.62, 125.00, 121.01, 83.31, 52.18, 38.52. IR (film): ν = 2925, 1715, 1595, 1478, 1441, 1281 cm^-1. HRMS: m/z calcd for C₁₆H₁₄O₃: 254.0946; found: 254.0941.