Issue 19, 2023

Photoinduced desaturative β-C(sp3)–H amidation of N-phenylpiperidine with phthalimide driven by electron donor–acceptor complexes

Abstract

A photoinduced desaturative β-C(sp3)–H bond amidation of N-phenylpiperidine using phthalimide as an aminating source enabled by an electron donor–acceptor (EDA) complex has been explored. This protocol avoids the use of high temperatures, transition metals and photosensitizers required for traditional C(sp3)–H functionalization, providing an environmentally friendly, simple and efficient protocol for accessing β-C(sp2)–H amidation piperidine derivatives. Additionally, the obtained products can be further modified and transformed into enamines by treatment with hydrazine.

Graphical abstract: Photoinduced desaturative β-C(sp3)–H amidation of N-phenylpiperidine with phthalimide driven by electron donor–acceptor complexes

Supplementary files

Article information

Article type
Research Article
Submitted
06 iyl 2023
Accepted
15 avq 2023
First published
23 avq 2023

Org. Chem. Front., 2023,10, 4758-4763

Photoinduced desaturative β-C(sp3)–H amidation of N-phenylpiperidine with phthalimide driven by electron donor–acceptor complexes

B. Sun, Y. Jiang, P. Huang, P. Li, C. Lv, Y. Xu, J. Wang and C. Jin, Org. Chem. Front., 2023, 10, 4758 DOI: 10.1039/D3QO01030A

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