Formation of C–O Bond via Cross-Dehydrogenative Coupling between Isochroman and Oxime under Metal-Free Oxidation Conditions

Abstract

DDQ-mediated C–O bond formation through cross-dehydrogenative coupling (CDC) reaction without any metal catalyst under mild conditions was developed. Series of isochromans and oximes could be employed as substrates, and the products were ­obtained in good yields.

Key words

cross-dehydrogenative coupling - C–H activation - DDQ - metal-free - oxidation

• Reference and Notes

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• 11 Typical Analytical Data of the Products Compound 3a: colorless oil; yield 85%. IR (neat): ν = 2939, 1740, 1492, 1316, 1208, 1096, 928, 748 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 8.15 (s, 1 H), 7.58 (d, J = 8.0 Hz, 2 H), 7.34 (d, J = 8.0 Hz, 3 H), 7.31–7.25 (m, 2 H), 7.17 (d, J = 8.0 Hz, 1 H), 6.36 (s, 1 H), 4.18 (td, J ₁ = 11.8 Hz, J ₂ = 3.2 Hz, 1 H), 4.03–3.98 (m, 1 H), 3.12–3.03 (m, 1 H), 2.65 (dd, J ₁ = 16.4 Hz, J ₂ = 2.0 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 150.64, 134.82, 131.81, 131.74, 130.09, 128.58, 128.48, 127.87, 127.35, 126.34, 99.10, 58.36, 27.75. HRMS (EI): m/z [M]⁺ calcd for C₁₆H₁₅NO₂: 253.1103; found: 253.1105. Compound 3i: blue oil; yield 77%. IR (neat): ν = 2935, 1711, 1493, 1274, 1095, 984, 922, 746 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.74–7.72 (m, 2 H), 7.37–7.35 (m, 4 H), 7.30–7.23 (m, 2 H), 7.17 (d, J = 8.0 Hz, 1 H), 6.40 (s, 1 H), 4.18 (td, J ₁ = 11.7 Hz, J ₂ = 3.5 Hz, 1 H), 4.02–3.98 (m, 1 H), 3.11–3.03 (m, 1 H), 2.65 (d, J = 16.0 Hz, 1 H), 2.25 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 156.48, 136.22, 134.86, 132.23, 129.21, 128.36, 128.25, 128.03, 126.27, 126.18, 98.98, 58.43, 27.85, 13.20. HRMS (EI): m/z [M]⁺ calcd for C₁₇H₁₇NO₂: 267.1259; found: 267.1257. Compound 3p: yellow solid; yield 44%. IR (neat): ν = 2971, 1700, 1590, 1486, 1244, 1005, 918, 750 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.92 (s, 1 H), 7.88 (t, J = 6.8 Hz, 2 H), 7.55–7.41 (m, 7 H), 7.28 (t, J = 8.0 Hz, 1 H), 7.14–7.11 (m, 2 H), 6.84 (s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 150.41, 150.13, 132.36, 131.87, 130.90, 130.45, 130.10, 129.53, 129.22, 128.76, 127.88, 127.45, 127.15, 124.52, 122.82, 122.40, 121.89, 120.94, 118.31, 99.80. HRMS (EI): m/z [M]⁺ calcd for C₂₀H₁₄BrNO₂: 379.0208; found: 379.0206.