Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

Jialin Zeng, Morio Naito, Takeru Torigoe, Masahiro Yamanaka, Yoichiro Kuninobu

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

Original languageEnglish
Pages (from-to)3485-3489
Number of pages5
JournalOrganic letters
Volume22
Issue number9
DOIs
Publication statusPublished - May 1 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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