80866-57-5Relevant academic research and scientific papers
Palladium(0)-catalyzed addition of Me3SnSnMe3 to alkyl 2-alkynoates and N,N-dimethyl-2-alkynamides. Facile preparation of alkyl (Z)- and (E)-2,3-bis(trimethylstannyl)-2-alkenoates and (E)-N,N-dimethyl-2,3-bis(trimethylstannyl)-2-alkenamides
Piers, Edward,Skerlj, Renato T.
, p. 2468 - 2482 (2007/10/02)
Treatment (tetrahydrofuran (THF), room temperature or reflux) of the alkyl 2-alkynoates 9-26 with (Me3Sn)2 in the presence of a Pd(0) catalyst ((Ph3P)4Pd) provides good to excellent yields of the corresponding alkyl (Z)-2,3-bis(trimethylstannyl)-2-alkenoates 47-64.The latter substances are thermally labile and, as demonstrated by a number of examples, are transformed upon heating (75-95 deg C) into the thermodynamically more stable E isomers.The Pd(0)-catalyzed addition of (Me3Sn)2 to N,N-dimethyl-2-alkynamides 44-46 is quite slow and the initially formed products (Z)-N,N -dimethyl-2,3-bis(trimethylstannyl)-2-alkenamides) rearrange to the corresponding E isomers at room temperature.
Convenient Synthesis of Alkyl (Z)- and (E)-2,3-Bis(trimethylstannyl)alk-2-enoates and N,N-Dimethyl (E)-2,3-Bis(trimethylstannyl)alk-2-enamides
Piers, Edward,Skerlj, Renato T.
, p. 626 - 627 (2007/10/02)
Palladium(0)-catalysed addition of (Me3Sn)2 to the α,β-acetylenic esters (1a-n) and amides (4a-d) provides the (Z)-2,3-bis)trimethylstannyl)alk-2-enoates (2a-n) and the (E)-2,3-bis(trimethylstannyl)alk-2-enamides (6a-d), respectively; thermolysis of (2a-h
