Synthesis of 3,5-disubstituted piperazinones via palladium(II)-catalyzed amination

Synlett

Volumn , Issue 13, 2006, Pages 2133-2135

  Ferber, Benoit ^a   Prestat, Guillaume ^a   Vogel, Sophie ^a   Madec, David ^a   Poli, Giovanni ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Amination; Palladium; Piperazinones; Ring closure; Stereoselectivity

Indexed keywords

LITHIUM CHLORIDE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; OXIDATION; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33748274686     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948208     Document Type: Article

References (17)

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12. 2 can be used since the cyclized organopalladium intermediate evolves via deacetoxypalladation rather than dehydropalladation.
13. 4 and concentrated under reduced pressure. Flash chromatography gave the pure piperazinone as a pale yellow oil (376 mg, 98%). Spectral data were in agreement with those previously reported by us. See ref. 8.
14. In the absence of palladium sources, quantitative recovery of starting material is observed.
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17. An equimolar mixture of the isolated piperazinone trans-12 and its precursor 6 was deliberately chosen for this test in order to reproduce the original reaction conditions. Indeed, interaction between the precursor and the catalytic system, such as reduction to a Pd(0) species, cannot be ruled out.