Xie, Lan-Gui published the artcileTertiary amine synthesis via reductive coupling of amides with Grignard reagents, Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Chemical Science (2017), 8(11), 7492-7497, database is CAplus and MEDLINE.
A new iridium catalyzed reductive coupling reaction of Grignard reagents R1MgX (R1 = Me, H2C:CH, Me3SiCH2, n-C5H11, PhCH2, etc.; X = Cl, Br) and tertiary amides R2C(O)NR3R4 (R2 = Ph, 4-MeOC6H4, 2-furyl, etc.; R3R4N = 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, etc; R3 = Me, MeO, Ph, PhCH2, R4 = Me; etc.) affording functionalised tertiary amine products R1R2CHNR3R4 via an efficient and tech.-simple one-pot, two-stage exptl. protocol, is reported. The reaction, which can be carried out on gram-scale using as little as 1 mol% Vaska’s complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane as the terminal reductant for the initial reductive activation step, tolerates a broad range of tertiary amides from (hetero)aromatic to aliphatic (branched, unbranched and formyl) and a wide variety of alkyl (linear, branched), vinyl, alkynyl and (hetero)aryl Grignard reagents. The new methodol. has been applied directly to bioactive mol. synthesis and the high chemoselectivity of the reductive coupling of amide has been exploited in late stage functionalization of drug mols. This reductive functionalisation of tertiary amides provides a new and practical solution to tertiary amine synthesis.
Chemical Science published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C12H9NO, Recommanded Product: (E)-1-Cinnamylpiperazine.
Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics