A Palladium-Catalyzed Borylation/Silica Gel Promoted Hydrolysis Sequence for the Synthesis of Hydroquinine-6′-Boric Acid and Its Applications

Hydroquinine-6′-boric acid was first synthesized via a palladium-catalyzed borylation/silica gel promoted hydrolysis sequence of hydroquinine-derived triflate and bis­(pinacolato)­diboron. The newly designed chiral building block was subjected to the Suzuki–Miyaura cross-coupling reaction, Petasis r...

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Published inJournal of organic chemistry Vol. 88; no. 15; pp. 11284 - 11298
Main Authors Liang, Wei, Chen, Zheng-Jun, Ran, Long-Hao, Chen, Lin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.08.2023
American Chemical Society (ACS)
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
hydrolysis
organic chemistry
Physical Sciences
Science & Technology
silica gel
Suzuki reaction
BORONIC ACIDS
CINCHONA ALKALOIDS
DEOXYFLUORINATION
QUININE
DERIVATIVES
SALTS
TRANSFORMATIONS
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Summary:Hydroquinine-6′-boric acid was first synthesized via a palladium-catalyzed borylation/silica gel promoted hydrolysis sequence of hydroquinine-derived triflate and bis­(pinacolato)­diboron. The newly designed chiral building block was subjected to the Suzuki–Miyaura cross-coupling reaction, Petasis reaction, and selenylation reaction, respectively, and all these reactions worked well to afford the corresponding 6′-functionalized hydroquinines with satisfactory results, demonstrating its extraordinary application potency.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c00774