TsOH-catalyzed dehydroxylative cross-coupling of alcohols with phenols: rapid access to propofol derivatives

Modification of the parent structure of molecules often alters their physicochemical properties and biological activities. Herein, a practical, efficient, and highly regioselective C-H alkylation of phenols with alcohols via dehydroxylative cross-coupling was developed to produce para -alkylated phe...

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Bibliographic Details
Published in:RSC advances 2024-08, Vol.14 (37), p.26857-26862
Main Authors: Liang, Yuqiu, Liu, Chengxiu, Li, Youchun, Ouyang, Lu
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Biological properties
Coupling (molecular)
Cross coupling
Molecular structure
Phenols
Reagents
Regioselectivity
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Summary:Modification of the parent structure of molecules often alters their physicochemical properties and biological activities. Herein, a practical, efficient, and highly regioselective C-H alkylation of phenols with alcohols via dehydroxylative cross-coupling was developed to produce para -alkylated phenols with excellent regioselectivities and yields, using which propofol derivatives were rapidly synthesized. This process is performed under mild and simple conditions and is well-compatible with a variety of alcohols (secondary and tertiary benzylic alcohols as well as allyl alcohols) as alkylated agents. In addition, high aryl ether derivatives were also obtained using this catalytic system. Wide substrate scope (up to 43 examples); excellent regioselectivity with only para -alkylated product; simple reaction conditions with only TsOH as catalyst, high efficiency in excellent yield; using stable and low toxicity alcohols as alkylate.
ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra04674a