945773-25-1Relevant articles and documents
Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions
Chen, Qiang,Fu, Liyan,You, Jingwen,Nishihara, Yasushi
supporting information, p. 1560 - 1564 (2020/11/12)
Nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes under copper-free conditions is described. This newly developed method has a wide substrate scope, affording internal silylethynes in moderate to high yields. The formation of 1,3-diynes as homocoupled products and conjugate enones as carbonyl-retentive products were effectively suppressed.
Sterically Controlled Late-Stage C-H Alkynylation of Arenes
Mondal, Arup,Chen, Hao,Fl?mig, Lea,Wedi, Philipp,Van Gemmeren, Manuel
supporting information, p. 18662 - 18667 (2019/11/28)
Phenylacetylenes are key structural motifs in organic chemistry, which find widespread applications in bioactive molecules, synthetic intermediates, functional materials, and reagents. These molecules are typically prepared from prefunctionalized starting materials, e.g. using the Sonogashira coupling, or using directing group-based C-H activation strategies. While highly efficient, these approaches remain limited by their inherent selectivities for specific regioisomers. Herein we present a complementary approach based on an arene-limited nondirected C-H activation. The reaction is predominantly controlled by steric rather than electronic factors and thereby gives access to a complementary product spectrum with respect to traditional methods. A broad scope as well as the suitability of this protocol for late-stage functionalization are demonstrated.
Amide to Alkyne Interconversion via a Nickel/Copper-Catalyzed Deamidative Cross-Coupling of Aryl and Alkenyl Amides
Srimontree, Watchara,Chatupheeraphat, Adisak,Liao, Hsuan-Hung,Rueping, Magnus
, p. 3091 - 3094 (2017/06/23)
A nickel-catalyzed deamidative cross-coupling reaction of amides with terminal alkynes as coupling partners was disclosed. This newly developed methodology allows the direct interconversion of amides to alkynes and enables a facile route for C(sp2)-C(sp) bond formation in a straightforward and mild fashion.
Nickel-catalyzed alkynylation of anisoles via C-O bond cleavage
Tobisu, Mamoru,Takahira, Tsuyoshi,Ohtsuki, Akimichi,Chatani, Naoto
supporting information, p. 680 - 683 (2015/03/05)
A new cross-coupling reaction has been developed for the introduction of an alkyne moiety to an anisole derivative through C-O bond activation using an NHC ligand. This method has been used for direct alkynylation of a broad range of anisole derivatives a
Molecular machines: synthesis and characterization of two prototypes of molecular wheelbarrows
Rapenne, Gwéna?l,Jimenez-Bueno, Gorka
, p. 7018 - 7026 (2008/02/05)
Technomimetic molecules are molecules designed to imitate macroscopic objects at the molecular level, also transposing the motions that these objects are able to undergo. This article focuses on the synthesis of two polyaromatic hydrocarbons designed by analogy with macroscopic wheelbarrows. The molecular wheelbarrows are synthesized following a modular strategy based on sequential double Knoevenagel and Diels-Alder reactions. Our strategy allowed to easily vary the chemical nature of the handles, which is crucial for subsequent manipulation with an STM tip.