Copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts: a general approach to the synthesis of enamides was written by Bolshan, Yuri;Batey, Robert A.. And the article was included in Tetrahedron in 2010.Computed Properties of C6H13NO3 This article mentions the following:
Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides using a catalytic amount of Cu(OAc)2 under mild oxidative conditions. The air and water stable alkenyltrifluoroborate salts offer a practical alternative to the use of alkenyl halides and alkenylboronic acids as cross-coupling partners. A range of amides participate in the cross-coupling, including heterocyclic amides, imides, carbamates, benzamides, and acetamides. Optimization studies established two sets of conditions, best suited to either high pKa or low pKa amide substrates. Lower pKa amide substrates worked best using a dichloromethane solvent system in the presence of 4 Å mol. sieves, 10 mol % Cu(OAc)2, and 20 mol % N-methylimidazole. Higher pKa amide substrates worked best using a ligandless protocol using a 1:1 dichloromethane/DMSO solvent system in the presence of 4 Å mol. sieves and 10 mol % Cu(OAc)2. The cross-coupling reactions occur stereospecifically with retention of alkene configuration from the alkenyltrifluoroborate salt. The mild reaction conditions employed are tolerant of various functionalities, including nitro, acetals, alkyl and aryl halides, and α,β-unsaturated carbonyls. Finally, the importance of copper sources and the presence of minor impurities were investigated. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Computed Properties of C6H13NO3).
2,2-Diethoxyacetamide (cas: 61189-99-9) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Computed Properties of C6H13NO3
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics