Iron‐Catalyzed Cross‐Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)−S/Se Bond Formation

The C−X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron‐catalyzed cross‐dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)−X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyano...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 17; pp. 4016 - 4021
Main Authors Huang, Lu‐Shan, Han, Dong‐Yang, Xu, Da‐Zhen
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 03.09.2019
Wiley Subscription Services, Inc
Subjects
Chemical industry
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Coupling (molecular)
Cross-dehydrogenative coupling
C−S bond formation
Dehydrogenation
Iron
Natural products
Organic chemistry
Oxidation; Air
Oxygen
Physical Sciences
Pyrazolones
Science & Technology
Thiols
Cross-dehydrogenative coupling
3,3-DISUBSTITUTED OXINDOLES
ACTIVATION
C-S bond formation
Iron
Air
FUNCTIONALIZATION
C-C BOND
REGIOSELECTIVE SYNTHESIS
Oxidation
H BONDS
ORGANOCATALYZED SULFENYLATION
ANTIFUNGAL
ASYMMETRIC SULFENYLATION
PHYTOALEXINS
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Summary:The C−X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron‐catalyzed cross‐dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)−X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (molecular oxygen) was employed as an ideal green oxidant, thus promising broad application in chemical industry and modification of bioactive molecules.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900400