C-H functionalization by transition-metal-catalyst or in situ generated base

Research output: Contribution to journalReview article

Abstract

Direct functionalization of the C-H bond is a highly attractive method because it does not require any pre-functionalized starting materials. Therefore this method can be adopted to attain the atom-and step-economic synthesis of organic compounds. We recently developed novel C-H functionalization reactions using two strategies. The first strategy is transition-metal catalyzed C-H functionalization, which comprises the copper-catalyzed oxidative C(sp3)-H functionalization of 2-alkyl-N-arylbenzamides for the synthesis of N-aryl-isoindolinones. This method can be applied to various substituted substrates and the synthesis of bioactive compounds, indoprofen and DWP205190. It provides an efficient approach toward the construction of isoindolinone skeletons. The second strategy is an in situ generated basemediated C-H functionalization comprising the deprotonative silylation of C(sp)-H and C(sp2)-H bonds by the base generated in situ from trifluoromethyltrimethylsilane (CF3SiMe3) and its activator. In the C(sp)-H silylation of terminal alkynes, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) acts as both a solvent and activator; therefore no additional activator is required. Moreover, the preferential deprotonation of terminal alkynes using this system proceeds faster than the trifluoromethylation of ketones and esters.

Original languageEnglish
Pages (from-to)1243-1251
Number of pages9
JournalYakugaku Zasshi
Volume139
Issue number10
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • C-H functionalization
  • Copper
  • In situ generated base
  • Isoindolinone
  • Silylation

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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