106536-25-8Relevant academic research and scientific papers
Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative heck reactions
Zheng, Changwu,Wang, Dian,Stahl, Shannon S.
supporting information, p. 16496 - 16499,4 (2020/09/15)
Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene.
One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl) silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide
Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 1523 - 1530 (2007/10/03)
2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1,3-(E) and (Z)-dienes. Their (Z)→(E) isomerization by classical means fails or leads to their polymerization. It is shown that SO2 can isomerize 1-aryl-3-methyl-1,3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1,3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)→(E) isomerizations.
THE ONE-POT PALLADIUM CATALYZED WITTIG REACTION WITH ALLYLIC ALCOHOLS. SCOPE AND LIMITATIONS
Moreno-Manas, M.,Ortuno, R. M.,Prat, M.,Galan, M. A.
, p. 1003 - 1014 (2007/10/02)
Some allylic alcohols react with aldehydes and triphenylphosphine in a one-pot formal Wittig reaction under Pd0 catalysis.The method has been extended to cinnamyl alcohol, 1, 2-methyl-2-propen-1-ol, 7, and 3-buten-2-ol, 11, and to heterocyclic aldehydes.
