Regio- and Trans-Selective Ni-Catalyzed Coupling of Butadiene, Carbonyls, and Arylboronic Acids to Homoallylic Alcohols under Base-Free Conditions

We herein report a Ni-catalyzed three-component coupling of 1,3-butadiene, carbonyl compounds, and arylboronic acids as a general synthetic approach to 1,4-disubstituted homoallylic alcohols, an important class of compounds, which have previously not been straightforward to access. The reaction occu...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 7; pp. 2571 - 2577
Main Authors Li, Yu-Qing, Chen, Guang, Shi, Shi-Liang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.04.2021
Amer Chemical Soc
Subjects
ambient temperature
catalysts
Chemistry
Chemistry, Organic
feedstocks
ligands
Physical Sciences
regioselectivity
Science & Technology
REAGENTS
1,3-DIENES
CONJUGATED DIENES
ALLYLATION
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
CYCLIZATION
3-COMPONENT CONNECTION REACTION
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Summary:We herein report a Ni-catalyzed three-component coupling of 1,3-butadiene, carbonyl compounds, and arylboronic acids as a general synthetic approach to 1,4-disubstituted homoallylic alcohols, an important class of compounds, which have previously not been straightforward to access. The reaction occurs efficiently using a Ni­(cod)2 catalyst without any external base and ligand at ambient temperature and allows a highly regioselective and trans-selective 1,4-dicarbofunctionalization of feedstock butadiene in a single operation. This simple and practical protocol could apply to a comprehensive scope of substrates. The neutral conditions show extraordinary tolerance for even highly base-sensitive functional groups.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c00488