Two Catalytic Protocols for the Synthesis of CF2‐Containing Quinazolinones via Domino Reaction

Copper‐catalyzed and visible‐light catalytic difluoroalkylation reactions of N‐cyanamide alkenes have been developed. Various α‐bromodifluoromethyl substituted esters, amides and heterocycles were employed as the CF2 source. Both protocols are characterized by medium to high yields, good functional...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 366; no. 14; pp. 3181 - 3187
Main Authors Wei, Congyin, Yu, Zhiyou, Shi, Lei
Format Journal Article
LanguageEnglish
Published Heidelberg Wiley Subscription Services, Inc 16.07.2024
Subjects
Amides
Cascade chemical reactions
Catalysis
Chemical reactions
Chemical synthesis
Copper
Difluoroalkylation reactions
Domino reaction
Esters
Functional groups
Heterocycles
Photoredox catalysis
Quinazolinone
Unactivated alkenes
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Summary:Copper‐catalyzed and visible‐light catalytic difluoroalkylation reactions of N‐cyanamide alkenes have been developed. Various α‐bromodifluoromethyl substituted esters, amides and heterocycles were employed as the CF2 source. Both protocols are characterized by medium to high yields, good functional group compatibility, and applicable to gram‐scale synthesis. Comparable studies of copper catalysis and photoredox catalysis demonstrate minimal differences between the two protocols. Preliminary mechanism suggest that both transformations involve tandem radical cyclization process.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400491