Construction of the Oxazolidinone Framework from Propargylamine and CO2 in Air at Ambient Temperature: Catalytic Effect of a Gold Complex Featuring an L2/Z-Type Ligand

被引:28
作者
Inagaki, Fuyuhiko [1 ]
Maeda, Kakeru [1 ]
Nakazawa, Kenta [1 ]
Mukai, Chisato [1 ]
机构
[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan
关键词
Z-type ligands; Carboxylation; Carbon dioxide fixation; Gold; Heterocycles; DATIVE SIGMA-BOND; CARBON-DIOXIDE; CARBOXYLATION; ACID; REACTIVITY; PALLADIUM; AMINES; REARRANGEMENT; CYCLIZATION; ACTIVATION;
D O I
10.1002/ejoc.201800228
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The metal-catalyzed carboxylation of propargylamines with aerial CO2 at room temperature to form 5-methyleneoxazolidin-2-one derivatives has been developed. In this reaction, the catalyst [Au(dpb(F))]X featuring a Z-type ligand gave the best results, presumably due to the sigma-acceptance of the borane atom.
引用
收藏
页码:2972 / 2976
页数:5
相关论文
共 59 条
[1]   σ-Acceptor, Z-type ligands for transition metals [J].
Amgoune, Abderrahmane ;
Bourissou, Didier .
CHEMICAL COMMUNICATIONS, 2011, 47 (03) :859-871
[2]   Catalytic conversion of nitrogen to ammonia by an iron model complex [J].
Anderson, John S. ;
Rittle, Jonathan ;
Peters, Jonas C. .
NATURE, 2013, 501 (7465) :84-+
[3]   Conversion of Fe-NH2 to Fe-N2 with release of NH3 [J].
Anderson, John S. ;
Moret, Marc-Etienne ;
Peters, Jonas C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) :534-537
[4]  
[Anonymous], 2014, CORE WRITING TEAM CL
[5]   Palladium-catalysed sequential carboxylation-alkoxycarbonylation of acetylenic amines [J].
Bacchi, A ;
Chiusoli, GP ;
Costa, M ;
Gabriele, B ;
Righi, C ;
Salerno, G .
CHEMICAL COMMUNICATIONS, 1997, (13) :1209-1210
[6]   COMPARISON OF THE MONOAMINE-OXIDASE INHIBITING PROPERTIES OF 2 REVERSIBLE AND SELECTIVE MONOAMINE OXIDASE-A INHIBITORS MOCLOBEMIDE AND TOLOXATONE, AND ASSESSMENT OF THEIR EFFECT ON PSYCHOMETRIC PERFORMANCE IN HEALTHY-SUBJECTS [J].
BERLIN, I ;
ZIMMER, R ;
THIEDE, HM ;
PAYAN, C ;
HERGUETA, T ;
ROBIN, L ;
PUECH, AJ .
BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 1990, 30 (06) :805-816
[7]  
Boden T, 2017, NATL CO 2 EMISSIONS
[8]   Complexes of ambiphilic ligands: reactivity and catalytic applications [J].
Bouhadir, Ghenwa ;
Bourissou, Didier .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (04) :1065-1079
[9]   Transition metals as Lewis bases: "Z-type" boron ligands and metal-to-boron dative bonding [J].
Braunschweig, Holger ;
Dewhurst, Rian D. .
DALTON TRANSACTIONS, 2011, 40 (03) :549-558
[10]   Sequential reaction of carbon dioxide and carbon monoxide with acetylenic amines in the presence of a palladium catalyst [J].
Chiusoli, GP ;
Costa, M ;
Gabriele, B ;
Salerno, G .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :297-310