253684-52-5Relevant articles and documents
Stereospecific hydrodehalogenation of alkenyl bromides: A new approach to the synthesis of (E)-alkenes
Chelucci, Giorgio
supporting information, p. 4069 - 4072 (2014/04/03)
The pair NaBH4-TMEDA and catalytic PdCl2(PPh 3)2 in THF at room temperature is a mild and efficient system for the hydrodebromination of alkenyl bromides, providing a facile reduction procedure that allows completing the process advantageously, leading from aldehydes to (E)-alkenes. This journal is the Partner Organisations 2014.
The Stille Reaction of 1,1-Dibromo-1-alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes
Shen, Wang,Wang, Le
, p. 8873 - 8879 (2007/10/03)
The Stille reaction of 1,1-dibromo-1-alkenes 1 with aryl- and vinylstannanes produces different products depending on the reaction conditions. When the reaction is run in toluene or 1,4-dioxane with tris(2-furyl)phosphine (TFP) as the ligand, (Z)-bromoalkenes 2 are obtained stereospecifically in good to excellent yields with most substrates. However, 2-aryl-1,1-dibromo-1-alkenes (1e,1g) having an electron-donating methoxy group in the para- or ortho- position give poor yields. This method has been applied to the one-pot syntheses of stereospecifically trisubstituted alkenes 5. When the Stille reaction is conducted in a highly dipolar solvent (DMF), monobromides 2 and/or internal alkynes 4 are the products. The less reactive phenylstannane favors the formation of alkynes 4, regardless of which ligand is used. More reactive organostannanes (vinyl, furyl) require a very electron rich ligand, tris(4-methoxyphenyl)phosphine, for the formation of alkynes 4. This new method for internal alkyne preparation is general, requires very mild reaction conditions, and gives high yields.