1235968-71-4

Upstream product

• 111409-79-1 1-bromo-2-(triisopropylsilyl)acetylene 
• 352-13-6 4-flourophenylmagnesium bromide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 456-22-4 4-Fluorobenzoic acid 
• 403-43-0 4-fluorobenzoyl chloride 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 6485-79-6 chlorotriisopropylsilane 
• 1583-56-8 4-fluorobenzoyl fluoride 
• 350-46-9 4-Fluoronitrobenzene 
• 462-06-6 fluorobenzene 

Relevant academic research and scientific papers

Sterically Controlled Late-Stage C-H Alkynylation of Arenes

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.

Chemoselective Aerobic Cross-Dehydrogenative Coupling of Terminal Alkynes with Hydrosilanes by a Nanoporous Gold Catalyst

Aerobic cross-dehydrogenative coupling between terminal alkynes and hydrosilanes occurred in the presence of nanoporous gold catalyst under O2 atmosphere. A variety of alkynylsilanes were synthesized in good-to-high yields and the catalyst was easily recovered and reused many times. Furthermore, the chemoselective direct silyl protection of terminal acetylenes of alkynols over the hydroxyl groups was achieved with this catalytic system.

Evidence for metal-ligand cooperation in a Pd-PNF pincer-catalyzed cross-coupling

The first Pd-pincer complex bearing a halogen (fluorine) arm has been prepared via the base-assisted dearomatization of a phosphine-quinoline (P～N) ligand. This dearomatization is reversible and has been used to facilitate catalytic Sonogashira-type cross-coupling that, contrary to the typical mechanistic approach, is based on a metal-ligand cooperation mode.

Amide to Alkyne Interconversion via a Nickel/Copper-Catalyzed Deamidative Cross-Coupling of Aryl and Alkenyl Amides

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.

Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes

Described herein is a palladium-catalyzed cross-coupling reaction between nitroarenes and terminal alkynes, offering a facile method for C(sp2)-C(sp) bond formation. The utility of this protocol has been proven by the construction of polycyclic aromatic hydrocarbons (PAHs) and orthogonal cross-coupling.

Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions

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.