Catalyst‐Free, Air‐Mediated C(sp2)−H Alkylation of Cyclic Aldimines with Alkylboronic Acids

The air mediated radical alkylation of cyclic aldimines via autoxidation of alkylboronic acids has been realized under mild reaction conditions. By simply heating cyclic aldimines with alkylboronic acid using air as sole oxidant, this protocol provides a catalyst‐free access to a variety of alkylate...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 365; no. 24; pp. 4544 - 4549
Main Authors Zhang, Jie, Li, Xiaolan, Liao, Lieqiang, Liu, Haidong, Luo, Haiqing
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.12.2023
Wiley Subscription Services, Inc
Subjects
Air-mediated
Alkylation
Alkylboronic acids
Autoxidation
Catalyst-free
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
Cyclic aldimines
Oxidizing agents
Physical Sciences
Radical alkylation
Science & Technology
Thermal cycling
Air-mediated
C-H ALKYLATION
Catalyst-free
ASYMMETRIC ARYLATION
Cyclic aldimines
ARYLBORONIC ACIDS
BORONIC ACIDS
CROSS-COUPLING REACTIONS
AMINO-ACID
Radical alkylation
NUCLEOPHILIC ALLYLATION
ENANTIOSELECTIVE ALKYNYLATION
Alkylboronic acids
MOLECULAR-OXYGEN
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Summary:The air mediated radical alkylation of cyclic aldimines via autoxidation of alkylboronic acids has been realized under mild reaction conditions. By simply heating cyclic aldimines with alkylboronic acid using air as sole oxidant, this protocol provides a catalyst‐free access to a variety of alkylated cyclic aldimines with 21–91% yields. Preliminary mechanistic studies suggest that a radical pathway might be involved in the reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301093