Catalyst-Free Regio- and Stereoselective C(sp2)-H Chlorination of Enamides at Room Temperature

Meng Liang Deng, Meng Wei Sheng, Xu Kang Wen, Ruo Nan Cao, Meng Li, Teck Peng Loh*, Ming Zhu Lu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

We disclose herein a catalyst-free, room-temperature protocol for the highly regio- and stereoselective alkenyl C(sp2)-H chlorination of diverse enamides with commercially available, inexpensive N-chlorosuccinimide (NCS) as the electrophilic chlorinating reagent under exceedingly mild conditions. This operationally simple approach features a remarkably broad substrate scope and accommodates excellent functional group tolerance, affording a diverse range of synthetically valuable geometrically defined β-chlorinated enamides in high yields with an exclusive E configuration.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2025
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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