Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides

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 cro...

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Published inJournal of the American Chemical Society Vol. 143; no. 9; pp. 3536 - 3543
Main Authors Li, Zijian, Sun, Wenxuan, Wang, Xianxu, Li, Luyang, Zhang, Yong, Li, Chao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ELECTROLYSIS
C-H ALKYLATION
N-HYDROXYPHTHALIMIDE ESTERS
ACTIVATION
ALLYLATION
BOND FORMATION
ORGANIC HALIDES
BROMIDES
PRINCIPLES
TOSYLATES
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Summary: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(sp2)–C­(sp3) 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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c13093