Palladium-Catalyzed C−H Iodination of Arenes by Means of Sulfinyl Directing Groups

Hayate Saito, Keita Yamamoto, Yosuke Sumiya, Ling Jun Liu, Keisuke Nogi, Satoshi Maeda, Hideki Yorimitsu

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

C−H iodination of aromatic compounds has been accomplished with the aid of sulfinyl directing groups under palladium catalysis. The reaction proceeds selectively at the peri-position of polycyclic aryl sulfoxides or at the ortho-position of phenyl sulfoxides. The iodination products can be further converted via iterative catalytic cross-coupling at the expense of the C−I and C−S bonds. Computational studies suggest that peri-C−H palladation would proceed via a non-directed pathway, wherein neither of the sulfur nor oxygen atom of the sulfinyl group coordinates to the palladium before and at the transition state.

Original languageEnglish
Pages (from-to)2442-2446
Number of pages5
JournalChemistry - An Asian Journal
Volume15
Issue number16
DOIs
Publication statusPublished - Aug 17 2020
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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