All Non-Carbon B 3 NO 2 Exotic Heterocycles: Synthesis, Dynamics, and Catalysis

Christopher R. Opie, Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

The B 3 NO 2 six-membered heterocycle (1,3-dioxa-5-aza-2,4,6-triborinane=DATB), comprising three different non-carbon period 2 elements, has been recently demonstrated to be a powerful catalyst for dehydrative condensation of carboxylic acids and amines. The tedious synthesis of DATB, however, has significantly diminished its utility as a catalyst, and thus the inherent chemical properties of the ring system have remained virtually unexplored. Here, a general and facile synthetic strategy that harnesses a pyrimidine-containing scaffold for the reliable installation of boron atoms is disclosed, giving rise to a series of Pym-DATBs from inexpensive materials in a modular fashion. The identification of a soluble Pym-DATB derivative allowed for the investigation of the dynamic nature of the B 3 NO 2 ring system, revealing differential ring-closing and -opening behaviors depending on the medium. Readily accessible Pym-DATBs proved their utility as efficient catalysts for dehydrative amidation with broad substrate scope and functional-group tolerance, offering a general and practical catalytic alternative to reagent-driven amidation.

Original languageEnglish
Pages (from-to)4648-4653
Number of pages6
JournalChemistry - A European Journal
Volume25
Issue number18
DOIs
Publication statusPublished - 2019 Mar 27
Externally publishedYes

Keywords

  • amidation
  • boron
  • catalysis
  • heterocycles
  • triborinane

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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