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 dehydroxylative cross-coupling was developed to produce -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.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11343040 | PMC |
| http://dx.doi.org/10.1039/d4ra04674a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
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 dehydroxylative cross-coupling was developed to produce -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.
View Article and Find Full Text PDFTitanium-Mediated Dehydroxylative Cross-Coupling of Allylic Alcohols with Electron-Deficient Olefins.
Org Lett
February 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Herein we report a Ti(III)-mediated dehydroxylative cross-coupling reaction of allylic alcohols with electron-deficient olefins. This reaction is amenable to various synthetically versatile allylic alcohols, including geraniol and farnesol, providing a general method for dehydroxylative C-C bond formation. We demonstrated the reaction's utility by simplifying the syntheses of eight useful building blocks that are otherwise laborious to prepare.
View Article and Find Full Text PDFTitanium(IV)-Mediated Ring-Opening/Dehydroxylative Cross-Coupling of Diaryl-Substituted Methanols with Cyclopropanol Derivatives.
J Org Chem
November 2021
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
A titanium(IV)-mediated ring-opening/dehydroxylative cross-coupling of diaryl-substituted methanols with a cyclopropanol derivative was developed. The reactions proceeded efficiently to provide synthetically useful γ,γ-diaryl esters in moderate to good yields, which could be applied to the functionalization of complex molecules derived from bioactive fenofibrate and isoxepac and the synthesis of a precursor of Zoloft.
View Article and Find Full Text PDFElectrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides.
J Am Chem Soc
March 2021
Tsinghua Institute of Multidisciplinary Biomedical Research, Tsinghua University, Beijing 100084, China.
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp)-C(sp) bonds, in which free alcohols and aryl bromides-both readily available chemicals-can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
View Article and Find Full Text PDFRadical Dehydroxylative Alkylation of Tertiary Alcohols by Ti Catalysis.
J Am Chem Soc
September 2020
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China.
Deoxygenative radical C-C bond-forming reactions of alcohols are a long-standing challenge in synthetic chemistry, and the current methods rely on multistep procedures. Herein, we report a direct dehydroxylative radical alkylation reaction of tertiary alcohols. This new protocol shows the feasibility of generating tertiary carbon radicals from alcohols and offers an approach for the facile and precise construction of all-carbon quaternary centers.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!