Photochemical C(sp3)-H Activation for Diversity-Oriented Synthesis of 3-Functionalized Oxindoles.
J Org Chem
; 89(6): 4120-4127, 2024 Mar 15.
Article
en En
| MEDLINE
| ID: mdl-38439707
ABSTRACT
Heteroatom-adjacent C(sp3) radical cyclization of N-arylacrylamides provides a straightforward pathway to synthesize valuable 3-functionalized oxindoles. Traditional cyclization reactions normally require harsh conditions or transition-metal catalysts. Here, we developed a metal-free, diversity-oriented synthesis of 3-functionalized oxindoles via photochemically induced selective cleavage of C(sp3)-H bonds. A variety of 3-substituted oxindoles with functionalities such as ethers, polyhalogens, benzyl, and formyl groups can be obtained by a rational design. This strategy is characterized by its simple operation and mild conditions, aligning well with the developmental requirements for sustainable chemistry. The gram-scale continuous-flow synthesis and efficient construction of bioactive molecules highlight its practical utility.
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MEDLINE
Idioma:
En
Revista:
J Org Chem
/
J. org. chem
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Journal of organic chemistry
Año:
2024
Tipo del documento:
Article