Synthesis of Vinyl Ethers

Synthesis of Functionalized Aryl-vinyl Ethers as Building Blocks and Auxiliaries in Organic Synthesis

5- hydroxyisoquinoline undergoes a smooth reaction with alkyl propiolates in the presence of triphenylphosphine (15 mol%) to produce the corresponding (E)-alkyl 3-(isoquinolin-5-yloxy) acrylate in good yields. When the reaction was performed by 2-methyl 4-hydroxyquinoline and 3-nitro 4-hydroxypyridine, similar aryl vinyl ethers were obtained.

Triphenylphosphine mediated synthesis of functionalized aryl-vinyl ethers from7-hydroxy coumarin and methyl acetylene carboxylate

7-hydroxy coumarin undergoes neutral conditions with alkyl propiolates in the presence of triphenylphosphine, and bysubstituation the corresponding aryl vinyl ethers was obtained in good yields

synthesis of functionalized aryl-vinyl ethers as building blocks and auxiliaries in organic synthesis

Pd-catalyzed addition of boronic acids to ynol ethers: a highly regio- and stereoselective synthesis of trisubstituted vinyl ethers.

A Pd-catalyzed addition of boronic acids to ynol ethers has been realized, delivering trisubstituted vinyl ethers in good yields with perfect control of the regio- and stereoselectivity. The reaction proceeds under mild conditions and exhibits excellent functional group compatibility. Moreover, the resultant products can be converted into pentasubstituted benzenes via the tandem Diels-Alder/aro...

Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes.

Synthesis of substituted 1,3-dienes was achieved via gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.