Design, synthesis, and application of multiboron heterocycle to direct amidation catalyst

Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of a multiboron heterocycle and its application to a direct amidation catalyst are described. The heterocycle comprised of B3NO2is called DATB. The DATB-catalyzed direct amide formation is well suited for the synthesis of a wide range of amides, including previously intractable ones. The catalysis can also be applied to peptide synthesis and N-acylation of sulfoxi- mines. The most active DATB contains four boron atoms in its structure, and the detailed mecha- nistic study revealed their distinctive roles in the catalytic cycle, depending on the given chemical environment. A pyrimidine containing analog was also developed and evaluated as a more readily accessible amidation catalyst than the original one. The Pym-DATB is now available from a commercial vendor. Current trends and future perspective in the boron - catalyzed direct amidation are also discussed.

Original languageEnglish
Pages (from-to)971-978
Number of pages8
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume78
Issue number10
DOIs
Publication statusPublished - 2020 Oct 1
Externally publishedYes

Keywords

  • Amide
  • Boron
  • Boron heterocycle
  • Catalyst
  • Peptide
  • Sulfoximine

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Design, synthesis, and application of multiboron heterocycle to direct amidation catalyst'. Together they form a unique fingerprint.

Cite this