Palladium-Catalyzed Csp3–H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers

Wen-Li Qiao; Ling-Yan Shao; Ya-Hua Hu; Li-Hao Xing; Ke-Zuan Deng; Hong-Wei Liu; Dao-Hua Liao; Ya-Fei Ji

doi:10.1055/s-0036-1609346

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(09): 1249-1255
DOI: 10.1055/s-0036-1609346

letter

Palladium-Catalyzed Csp³–H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers

Wen-Li Qiao

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Ling-Yan Shao*

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Ya-Hua Hu

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Li-Hao Xing

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Ke-Zuan Deng

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Hong-Wei Liu

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Dao-Hua Liao

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

,

Ya-Fei Ji*

School of Pharmacy, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: shaoly520@163.com eMail: jyf@ecust.edu.cn

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Abstract

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Abstract

A palladium-catalyzed Csp³–H bond mono-aroyloxylation of O-alkyl substituted oxime ethers has been developed by using 2,4,6-trimethoxybenzaldoxime as an exo-type directing group with exclusive site-selectivity. With the wide range of masked aliphatic alcohol substrates and aromatic acid coupling partners, the protocol allows rapid access to various 2-alkyl substituted glycol derivatives in synthetically useful to good yields. The employed directing group is readily removed, accordingly affording valuable functionalized aliphatic alcohols. When the solvent from hybrid DCE/HFIP to CH₃CN, non-directed oxidative cross-coupling is observed between the electron-rich aromatic ring of substrates and aromatic acid partners.

Key words

palladium-catalysis - Csp³–H bond functionalization - aroyloxylation - masked aliphatic alcohol - oxidative cross-coupling

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Referenzen

References and Notes

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12 Synthesis of 3 and 4; General Procedure A mixture of substrate 1 (0.3 mmol), 2 (3.0 equiv), Pd(OAc)₂ (10 mol%) and K₂S₂O₈ (3.0 equiv), PhI(OAc)₂ (0.3 equiv) were dissolved in DCE/HFIP (3:1, v/v, 3 mL) in a Schlenk tube. The vial was tightly capped and stirred at 80 °C for 24 h. Upon completion, the mixture was dropped into saturated NaHCO₃ solution (30 mL) and the mixture was extracted with dichloromethane (3 × 25 mL), and the combined organic layers were dried over anhydrous MgSO₄. Finally, the solution was concentrated in vacuo to provide the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:1) to give the desired product 3 or 4. (E,Z)-2-(((2,4,6-Trimethoxybenzylidene)amino)oxy)heptyl 4-Methoxybenzoate (3h): Yield: 65%; yellow oil; E/Z = 5.67:1. ¹H NMR (400 MHz, CDCl₃): δ = 8.42 (s, 0.85 H, E-isomer), 8.41 (s, 0.15 H, Z-isomer), 8.01 (d, J = 9.2 Hz, 2 H), 6.88 (d, J = 8.8 Hz, 2 H), 6.10 (s, 2 H), 4.53–4.52 (m, 1 H), 4.50–4.45 (m, 2 H), 3.84 (s, 3 H), 3.82 (s, 3 H), 3.80 (s, 6 H), 1.83–1.69 (m, 2 H), 1.37–1.33 (m, 2 H), 1.33–1.32 (m, 2 H), 1.28–1.25 (m, 2 H), 0.88 (t, J = 5.7 Hz, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 166.4, 163.3, 162.3, 160.1 (2C), 144.2, 131.7 (2C), 122.9, 113.5 (2C), 102.8, 90.8 (2C), 80.3, 65.7, 56.0 (2C), 55.4, 55.3, 31.9, 30.9, 25.1, 22.6, 14.1; HRMS (ESI): m/z [M+ H]⁺ calcd. for C₂₅H₃₄NO₇ ⁺: 460.2335; found: 460.2331.

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