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Synlett 2018; 29(09): 1249-1255
DOI: 10.1055/s-0036-1609346
DOI: 10.1055/s-0036-1609346
letter
Palladium-Catalyzed Csp3–H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers
We gratefully thank the National Natural Science Foundation of China (Project Nos. 21476074 and 21676088) for financial support.Further Information
Publication History
Received: 03 January 2018
Accepted after revision: 20 February 2018
Publication Date:
14 March 2018 (online)
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-couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609346.
- Supporting Information
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