Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins

Yusuke Hara, Shunsuke Onodera, Takuya Kochi, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

We report here a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C-H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups. The reaction proceeded smoothly without using bases to give α-aryl ketones in high yields. Various nitrogen-containing aromatic rings and amide groups serve as directing groups. 3-Substituted isocoumarins can also be prepared by one-pot C-H functionalization/cyclization.

Original languageEnglish
Pages (from-to)4850-4853
Number of pages4
JournalOrganic Letters
Volume17
Issue number19
DOIs
Publication statusPublished - 2015 Oct 2

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Isocoumarins
Bearings (structural)
Rhodium
Carbonates
Cyclization
Ketones
Amides
ketones
carbonates
Nitrogen
synthesis
rhodium
amides
nitrogen
isocoumarin 3
rings

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins. / Hara, Yusuke; Onodera, Shunsuke; Kochi, Takuya; Kakiuchi, Fumitoshi.

In: Organic Letters, Vol. 17, No. 19, 02.10.2015, p. 4850-4853.

Research output: Contribution to journalArticle

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