1203447-52-2

Upstream product

• 13807-89-1 2-(4-methoxybenzyloxy)ethanol 
• 824-94-2 p-methoxybenzyl chloride 
• 72802-79-0 carbon-¹³C-tetrabromide 
• 121289-23-4 p-methoxybenzyloxyacetaldehyde 

Downstream Products

• 1203447-53-3 triisopropyl(3-(4-methoxybenzyloxy)prop-1-ynyl)silane 

Relevant academic research and scientific papers

Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents

Alkynes have found widespread applications in synthetic chemistry, biology, and materials sciences. In recent years, methods based on electrophilic alkynylation with hypervalent iodine reagents have made acetylene synthesis more flexible and efficient, but they lead to the formation of one equivalent of an iodoarene as side-product. Herein, a more efficient strategy involving a copper-catalyzed oxy-alkynylation of diazo compounds with ethynylbenziodoxol(on)e (EBX) reagents is described, which proceeds with generation of nitrogen gas as the only waste. This reaction is remarkable for its broad scope in both EBX reagents and diazo compounds. In addition, vinyl diazo compounds gave enynes selectively as single geometric isomers. The functional groups introduced during the transformation served as easy handles to access useful building blocks for synthetic and medicinal chemistry.

Organocatalytic Enantioselective 1,3-Difunctionalizations of Morita-Baylis-Hillman Carbonates

The in-situ-generated zwitterionic allylic ylides between Morita-Baylis-Hillman carbonates from isatins and chiral tertiary amine catalysts underwent highly regioselective and enantioselective 1,3-oxo-ethynylation or 1,3-amino-sulfenylation reactions with silyl ethynyl-1,2-benziodoxol-3(1H)-ones or N-(aryl or alkylthio)imides, respectively, giving densely functionalized products bearing a quaternary stereogenic center. An array of diversely structured scaffolds were efficiently constructed from the products, showing the synthetic versatility of the current catalytic strategy.

Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine

(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.

Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters

Hot alkyne! The in situ generation of ethynyl-1,2-benziodoxol-3(1H)-one (EBX) from a silyl-protected reagent by using TBAF is reported. EBX displayed exceptional acetylene transfer ability onto stabilized enolates (see scheme), even at -78 □°C. The mild reaction conditions allowed the first ethynylation reactions of linear keto, cyano, and nitro esters in high yields to give all-carbon quaternary centers or non-natural amino acids after selective reduction of the nitro group.

Direct alkynylation of indole and pyrrole heterocycles

Chemical Equitation Presentation Easy does it: The unique properties of benziodoxolone alkynyl periodinane l and gold catalysts have allowed the development of a high yielding, operationally simple (room temperature, no dry sol-vents or inert conditions, commercially available catalyst) reaction for the introduction of silylacetylenes on a large range of indole and pyrrole heterocycles with a wide range of functional groups (see scheme).