Preparation of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides.

Title

Preparation of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides.

Subject

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Description

A copper(I)-catalyzed procedure for the synthesis of 1,3-enynes, e.g., 99 % Et (Z)-5-phenyl-2-penten-4-ynoate from phenylacetylene and Et (Z)-3-iodoacrylate using 10 mol% [Cu(bipy)(PPh3)Br] and 2.0 equiv K2CO3 in toluene at 110° for 8 h, is reported. This method afforded a variety of enynes in good to excellent yields. This method tolerated a variety of functional groups, did not require the use of expensive additives, and was palladium-free. [on SciFinder(R)]

Creator

Venkataraman, Dhandapani; Bates, Craig G.; Saejueng, Pranorm.

Source

U.S. Pat. Appl. Publ.

Date

2005

Rights

Application: US

Relation

Vinyl compounds Role: RCT (Reactant), RACT (Reactant or reagent) (halo; stereoselective prepn. of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides); Crystal structure (of copper(I) phenanthroline phosphine complex nitrate); Stereoselective synthesis (stereoselective prepn. of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides); Alkenynes Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides); Cross-coupling reaction; Cross-coupling reaction catalysts (stereoselective; stereoselective prepn. of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides); Alkynes Role: RCT (Reactant), RACT (Reactant or reagent) (α-; stereoselective prepn. of enynes via copper-catalyzed stereoselective cross-coupling of terminal alkynes with vinyl iodides)

Language

written in English

Identifier

2005-115502