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

Hua-Feng He; Kai Wang; Bo Xing; Guorong Sheng; Tingxuan Ma; Weiliang Bao

doi:10.1055/s-0032-1317960

Synlett, Table of Contents

Synlett 2013; 24(2): 211-214
DOI: 10.1055/s-0032-1317960

letter

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

Hua-Feng He

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

,

Kai Wang

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

,

Bo Xing

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

,

Guorong Sheng

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

,

Tingxuan Ma

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

,

Weiliang Bao*

Department of Chemistry, Xi Xi Campus, Zhejiang University, Hangzhou, Zhejiang 310028, P. R. of China Fax: +86(571)88273814 Email: wlbao@css.zju.edu.cn

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Abstract

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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

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References

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.

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