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Upstream product

• 109431-70-1 4-phenylbut-3-yn-2-yl acetate 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 591-50-4 iodobenzene 
• 622-76-4 1-phenyl-1-butyne 

Relevant academic research and scientific papers

α-Haloenones from secondary alkynols

α-Iodoenones and α-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol (1) was converted to (Z)-4-iodo-4-hexen-3-one (2) in 85-95% yields w

Direct Conversion of Internal Alkynes into α-Iodoenones: One-Step Collaborative Iodination and Oxidation

The reaction of an internal alkyne with 2,6-dichloropyridine N-oxide, a nucleophilic oxidant, and electrophilic N-iodosuccinimide (NIS) simultaneously enables the direct access to versatile α-iodoenones. Electronically biased internal alkynes undergo the one-step transformation with excellent regioselectivities and with practical Z/E ratios. In comparison to the related oxidative gold catalysis using pyridine N-oxides, this reaction employs NIS as the stoichiometric ynophile instead of the soft acidic noble metal catalyst and affords products featuring an additional versatile C-I bond. Similar strategies for replacing ynophilic cationic gold(I) complexes in oxidative gold catalysis with likewise ynophilic stoichiometric electrophiles would enable the development of new synthetic methods.

SYNTHESIS OF ALPHA-HALO ENONES AND ENALS

A method for preparing an α-halo enal or enone from an unprotected propargyl alcohol and an electrophilic halogen source catalyzed by the combination of a gold catalyst complex and a metal co-catalyst complex is disclosed. The method can be further enhanced by addition of an additive that facilitates suppression of a des-halo derivative.

Practical synthesis of linear α-iodo/bromo-α,β-unsaturated aldehydes/ketones from propargylic alcohols via Au/Mo bimetallic catalysis

Image Presented An efficient synthesis of α-iodo/bromo-α, β-unsaturated aldehydes/ketones directly from propargylic alcohols is described. This reaction is catalyzed collaboratively by two metal complexes, Ph3PAuNTf2 and MoO2/s

Gold-catalyzed efficient preparation of linear α-haloenones from propargylic acetates

Versatile linear α-iodo- and α-bromoenones are prepared efficiently from readily accessible propargylic acetates using 2 mol % of Au(PPh3)NTf2. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of propargylic acetates derived from aliphatic aldehydes.

Gold-catalyzed efficient preparation of linear α-lodoenones from propargylic acetates

Only 2 mol % of Au(PPh3)NTf2 is needed to convert readily accessible propargylic acetates into versatile linear α-iodoenones in good to excellent yields. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of aliphatic propargylic acetates derived from aldehydes.