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

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

研究成果: Article査読

27 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4648-4653
ページ数6
ジャーナルChemistry - A European Journal
25
18
DOI
出版ステータスPublished - 2019 3月 27
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

フィンガープリント

「All Non-Carbon B 3 NO 2 Exotic Heterocycles: Synthesis, Dynamics, and Catalysis」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル