Lewis Acid Mediated [3+2] Coupling of Masked Benzoquinones with Styrenes: Facile Synthesis of 2,3-Dihydrobenzofurans

Shivangi Sharma; Santosh Kumar Reddy Parumala; Rama Krishna Peddinti

doi:10.1055/s-0036-1588622

Synlett, Table of Contents

Synlett 2017; 28(02): 239-244
DOI: 10.1055/s-0036-1588622

letter

Lewis Acid Mediated [3+2] Coupling of Masked Benzoquinones with Styrenes: Facile Synthesis of 2,3-Dihydrobenzofurans

Authors

Shivangi Sharma

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India Email: rkpedfcy@iitr.ac.in Email: ramakpeddinti@gmail.com
Santosh Kumar Reddy Parumala

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India Email: rkpedfcy@iitr.ac.in Email: ramakpeddinti@gmail.com
Rama Krishna Peddinti*

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India Email: rkpedfcy@iitr.ac.in Email: ramakpeddinti@gmail.com

Abstract

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Abstract

We have developed an efficient, simple, mild, and rapid method for the construction of dihydrobenzofuran derivatives by the [3+2] coupling of masked o-benzoquinones with styrene derivatives triggered by boron trifluoride diethyl etherate. This new [3+2] coupling protocol proceeds smoothly to afford dihydrobenzofuran derivatives in good to high yields within one minute. The method was extended to cycloaddition of p-benzoquinone monoketal with styrenes.

Key words

hypervalent iodine reagents - oxidation - dearomatization - benzoquinone monoketals - cycloaddition - benzofurans

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References

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17 2,3-Dihydrobenzofuran Derivatives 4; General Procedure PhI(OAc)₂ (0.177 g, 0.55 mmol, 1.1 equiv) was added to a solution of the appropriate guaiacol derivative 1 (0.5 mmol) in MeOH (5 mL), and the mixture was stirred for 5 min at r.t. After generation of the o-benzoquinone monoketal 2, as indicated by a yellow color of the solution, the MeOH was removed under reduced pressure and the residue was dissolved in CH₂Cl₂. The solution was cooled to –30 °C and the appropriate alkene (1 mmol) and BF₃·OEt₂ (1 mmol) were added sequentially. When the reaction was complete (TLC), it was quenched with sat. aq NaHCO₃ and the mixture was extracted with CH₂Cl₂ (2 × 15 mL). The combined organic phases were dried (Na₂SO₄), filtered, and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 1–2% EtOAc–hexanes). 5-Bromo-7-methoxy-2-phenyl-2,3-dihydrobenzofuran (4aa) Viscous yellow liquid; yield: 0.124 g (82%). IR (KBr): 2928, 2851, 1615, 1484, 1293, 1270, 1197, 1094, 763, 699 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.41–7.29 (m, 5 H), 6.95–6.94 (m, 1 H), 6.91–6.90 (m, 1 H), 5.80 (t, J = 9.0 Hz, 1 H), 3.87 (s, 3 H), 3.61 (dd, J = 9.5, 15.5 Hz, 1 H), 3.23 (dd, J = 8.5, 16.0 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 147.1 (C), 144.7 (C), 140.9 (C), 129.1 (C), 128.5 (CH), 128.1 (CH), 125.8 (CH), 119.8 (CH), 114.6 (CH), 112.3 (C), 85.1 (CH), 56.1 (OCH₃), 38.5 (CH₂). 5-Bromo-2-(4-isopropylphenyl)-7-methoxy-2,3-dihydrobenzofuran (4ah) Viscous colorless liquid; yield: 0.140 g (81%). IR (KBr): 2959, 2931, 1615, 1483, 1293, 1195, 1095, 946, 831, 776 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.30 (d, J = 8.0 Hz, 2 H), 7.20 (d, J = 7.5 Hz, 2 H), 6.92 (s, 1 H), 6.88 (s, 1 H), 5.75 (t, J = 8.5 Hz, 1 H), 3.83 (s, 3 H), 3.56 (dd, J = 9.0, 15.5 Hz, 1 H), 3.23 (dd, J = 8.5, 16.0 Hz, 1 H), 2.89 (quint, J = 6.5 Hz, 1 H), 1.23 (s, 3 H), 1.22 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 149.0 (C), 147.2 (C), 144.8 (C), 138.3 (C), 129.3 (C), 126.6 (CH), 126.1 (CH), 119.9 (CH), 114.8 (CH), 112.2 (C), 85.2 (CH), 56.2 (OCH₃), 38.3 (CH₂), 33.8 (CH₃), 23.9 (CH₃). 2-(4-Bromophenyl)-5-chloro-7-methoxy-2,3-dihydrobenzofuran (4bc) Viscous colorless liquid; yield: 0.135 g (80%). IR (KBr): 2931, 2840, 1617, 1485, 1297, 1196, 1097, 1072, 946, 826, 790 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.38 (d, J = 8.0 Hz, 2 H), 7.17 (d, J = 7.5 Hz, 2 H), 6.69 (s, 1 H), 6.67 (s, 1 H), 5.66 (t, J = 8.5 Hz, 1 H), 3.77 (s, 3 H), 3.50 (dd, J = 10.0, 16.0 Hz, 1 H), 3.06 (dd, J = 8.5, 15.5 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 146.4 (C), 144.4 (C), 140.1 (C), 131.7 (CH), 128.1 (C), 127.5 (CH), 125.6 (C), 122.0 (C), 116.9 (CH), 111.9 (CH), 84.3 (CH), 56.1 (OCH₃), 38.5 (CH₂). 5-Chloro-7-methoxy-2-methyl-2-phenyl-2,3-dihydrobenzofuran (4bg) Viscous colorless liquid; yield: 0.092 g (67%). IR (KBr): 2981, 2925, 1616, 1487, 1444, 1301, 1233, 1099, 838, 764 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.46 (d, J = 8.0 Hz, 2 H), 7.34 (t, J = 7.5 Hz, 2 H), 7.24–7.28 (m, 1 H), 6.76 (s, 1 H), 6.74 (s, 1 H), 3.91 (s, 3 H), 3.40 (q, J = 15.5 Hz, 2 H), 1.81 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 146.0 (C), 145.9 (C), 144.6 (C), 128.4 (CH), 127.2 (CH), 125.2 (C), 124.4 (CH), 117.1 (CH), 111.9 (CH), 90.5 (C), 56.2 (OCH₃), 45.0 (CH₂), 29.2 (CH₃). 5-Iodo-7-methoxy-2-methyl-2-phenyl-2,3-dihydrobenzofuran (4cg) Viscous colorless liquid; yield: 0.126 g (69%). IR (KBr): 2966, 1609, 1482, 1294, 1141, 1093, 832, 761 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.47 (d, J = 7.5 Hz, 2 H), 7.36 (t, J = 7.5 Hz, 2 H), 7.29–7.26 (m, 1 H), 7.09 (s, 1 H), 7.07 (s, 1 H), 3.92 (s, 3 H), 3.42 (q, J = 15.5 Hz, 2 H), 1.83 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 147.2 (C), 145.9 (C), 145.3 (C), 129.7 (C), 128.3 (CH), 127.2 (CH), 126.1 (CH), 124.4 (CH), 120.2 (CH), 90.5 (C), 81.4 (C), 56.2 (OCH₃), 44.7 (CH₂), 29.1 (CH₃). trans-5-Iodo-7-methoxy-3-methyl-2-phenyl-2,3-dihydrobenzofuran (4ci) Viscous colorless liquid; yield: 0.130 g (71%). IR (KBr): 2960, 1610, 1479, 1279, 1195, 1078, 965, 833 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.42–7.32 (m, 5 H), 7.08 (s, 2 H), 5.22 (d, J = 9.0 Hz, 1 H), 3.51 (s, 3 H), 3.48 (quint, J = 7.0 Hz, 1 H), 1.41 (d, J = 6.5 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 147.5 (C), 145.1 (C), 139.9 (C), 135.2 (C), 128.6 (CH), 128.4 (CH), 126.2 (CH), 125.0 (CH), 120.5 (CH), 93.3 (CH), 81.9 (C), 56.2 (OCH₃), 45.7 (CH), 18.0 (CH₃).
18 For the stereochemistry of similar compounds, see ref. 6b and: Juhász L, Szilágyi L, Antus S, Visy J, Zsila F, Simonyi M. Tetrahedron 2002; 58: 4261

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