4.4 Article

Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue

期刊

SYNLETT
卷 33, 期 6, 页码 531-545

出版社

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1719857

关键词

annulation; aryne; cycloaddition; sequential reactions; triptycene; ynolates

资金

  1. Japan Society for the Promotion of Science (JSPS KAKENHI) [JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP20K21198, JP20K15283]
  2. NAGASE Science Technology Foundation
  3. Asahi Glass Foundation
  4. Qdai-jump Research Program Wakaba Challenge at Kyushu University
  5. IRCCS Fusion Emergent Research Program

向作者/读者索取更多资源

This paper describes the ynolate-initiated cycloaddition reaction to form a variety of carbocycles and heterocycles. Ynolates have the ability to achieve double addition and can perform formal [n+1]-type annulations, demonstrating their high-energy performance. The synthetic applications of these methods, including natural products synthesis, are discussed as well.
In this paper, ynolate-initiated cycloaddition (annulation) to form a range of carbocycles and heterocycles is described. Ynolates consist of a ketene anion equivalent, which contains both nucleophilic and electrophilic moieties, and a carbodianion equivalent that achieves double addition. Hence, in addition to the usual [n+2] cycloaddition, ynolates can perform formal [n+1]-type annulations. Their high-energy performance has been demonstrated by their triple addition to arynes to generate triptycenes, in which the C-C triple bond of ynolates is cleaved. The synthetic applications of these methods, including natural products synthesis, are also described.

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