125847-87-2Relevant articles and documents
Palladium-Catalyzed Direct Arylation of C(sp3)-H Bonds of α-Cyano Aliphatic Amides
Reddy, M. Damoder,Watkins, E. Blake
, p. 11447 - 11459 (2015/12/05)
Pd(OAc)2-catalyzed arylation of C(sp3)-H bonds in α-cyano-α-methyl aliphatic amides is achieved in the presence of 8-aminoquinoline, as a removable directing group, using Mn(OAc)2 and Na2CO3. The current strategy enables the placement of an aryl/heteroaryl group at the β-position of α-cyano aliphatic acids for the first time. Wide functional group tolerance and easily accessible starting materials provide an efficient protocol for the synthesis of arylated α-cyano amides. Furthermore, the synthetic utility of the products has been demonstrated by their efficient conversions to medicinally important α,α-dialkylated acid and β-amino acid derivatives.
Cobalt Carbonyl Mediated Michael Addition: Direct Synthesis of Esters Containing Other Functional Groups from Activated Olefins
Sisak, Attila,Ungvary, Ferenc,Marko, Laszlo
, p. 2508 - 2513 (2007/10/02)
Hydrocarbalkoxylation of acrylonitrile with stoichiometric amounts of alcohols in the presence of catalytic amounts of Co2(CO)8 and pyridine bases leads to 2,4-dicyano-2-methylbutanoic acid esters.The yield of these Michael adducts shows a maximum as a function of the pyridine/cobalt ratio.Analogues reactions using equimolar amounts of alcohol, acrylonitrile, and an other activated olefin result in products with at least three different functional groups.Acrylonitrile with pyH gives (1-cyanoethyl)cobalt tetracarbonyl, which is proposed to be the key intermediate of the hydrocarbalkoxylation.This complex may be deprotonated to a "Michael donor" anion, i.e. the Michael adducts are most probably formed in a cobalt-mediated way.The above catalytic system promoted also the Michael addition of some C-H acids to activated olefins under atmospheric conditions.
