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

研究成果: Review article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1243-1251
ページ数9
ジャーナルYakugaku Zasshi
139
10
DOI
出版ステータスPublished - 2019

ASJC Scopus subject areas

  • 薬理学
  • 薬科学

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