99299-73-7

Upstream product

• 150-76-5 4-methoxy-phenol 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 1622092-94-7 (2-bromo-4-methoxyphenoxy)(tert-butyl)dimethylsilane 
• 1622092-95-8 tert-butyl{4-methoxy-2-[(trimethylsilyl)ethynyl]phenoxy}-dimethylsilane 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 1622092-54-9 2-(2-ethynyl-4-methoxyphenoxy)ethyl 4-bromobenzenesulfonate 
• 1622092-82-3 (E)-(6-methoxy-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate 
• 39581-55-0 5-methoxy-benzofuran-3-one 

Relevant academic research and scientific papers

A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones

The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.

Cyclization of gold acetylides: Synthesis of vinyl sulfonates via gold vinylidene complexes

Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example. Gold vinylidene intermediates are generated by the cyclization of gold acetylides that carry a sulfonate leaving group. This result demonstrates for the first time that the formation of these species is not restricted to a dual activation mode. The cyclization products obtained herein contain a vinyl sulfonate moiety, which makes them useful building blocks for cross-coupling reactions.

Halocarbon Chemistry. !. (2-Hydroxyaryl)acetylenes from Haloethyl Aryl Ethers. A New O to C Rearrangement.

A new base-induced (BuLi) oxygen-to carbon rearrangement is described which involves the direct conversion of phenyl tetra(or tri)haloethyl ethers and the related intermediate phenoxyalkynes to the corresponding 1-(2-hydroxyphenyl)alkynes in good to excel