910219-78-2

Upstream product

• 1234580-89-2 naphthalen-2-ylmethyl 3-phenylpropiolate 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 108-86-1 bromobenzene 
• 1592-38-7 2-Naphthalenemethanol 
• 536-74-3 phenylacetylene 
• 478282-11-0 1-(2-naphthyl)-3-phenyl-prop-2-yn-1-ol 
• 6738-06-3 phenylethynylmagnesium bromide 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 1416982-18-7 N,N,N-trimethyl-1-(naphthalen-2-yl)methanaminium trifluoromethanesulfonate 

Downstream Products

• 257904-77-1 2-(3-phenylpropa-1,2-dienyl)naphthalene 
• 1271054-68-2 1-(naphthalen-2-yl)-3-phenylbuta-1,2-diene 

Relevant academic research and scientific papers

Cu-Photoredox-catalyzed C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes

Visible-light-induced C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes has been developed. The activation of carboxylic acids as their redox-active ester derivatives was important for this decarboxylative alkynylation. The strategy established here facilitates the straightforward introduction of triple-bonded functional groups and avoids additional photocatalysts. A wide range of primary, secondary and tertiary acids can be converted into the target products; so this reaction exhibits a broad substrate scope and tolerance of functional groups. Mechanistic experiments suggested that this reaction may undergo a radical process. Under mild reaction conditions, a copper acetylide ligand as a photocatalyst delivered an electron to redox-active ester derivatives, and generated alkyl radicals. The radicals reacted with Cu(ii) to deliver a Cu(iii) complex, and then reductive elimination gave the products.

Palladium-Catalyzed Coupling of Terminal Alkynes with Benzyl Ammonium Salts

A highly efficient palladium-catalyzed Sonogashira coupling of benzylic ammonium salts with terminal alkynes is developed. This strategy provides a facile access to a series of internal alkyne derivatives in moderate to excellent yields via C-N bond cleavage and C(sp3)-C(sp) bond formation. The broad substrate scope and high functional group tolerance make this reaction attractive for organic synthesis.

Cleavage of C–C and C–O Bonds to Form C–C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates

A palladium-catalyzed cross-coupling reaction between C(sp) and C(sp3) centers was achieved in excellent yields via C–C bond cleavage and C–O bond cleavage. This procedure uses relatively stable acetylenic alcohols as reactants instead of unsta

Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates

Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

Decarboxylative benzylations of alkynes and ketones

Benzyl esters of propiolic and β-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

Ruthenium-catalyzed propargylic reduction of propargylic alcohols with silanes

Ru2 can do it! Substitution of the OH moiety in propargylic alcohols by hydride proceeds smoothly with triethylsilane by catalysis with the thiolate-bridged diruthenium complex 1 (see scheme; Cp* = η5-C5Me5). Th