54339-97-8Relevant academic research and scientific papers
Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate
He, Lu-Ying,Schulz-Senft, Mathias,Thiedemann, Birk,Linshoeft, Julian,Gates, Paul J.,Staubitz, Anne
, p. 2498 - 2502 (2015)
A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.
Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide
Plamont, Rémi,Graux, Lionel V.,Clavier, Hervé
supporting information, p. 1372 - 1376 (2018/04/02)
1,3-Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition-metal-based catalysts and Lewis acids. ZnI2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.
