Conjugated Dienyl Derivatives by Green Bisallylic Substitution: Synthetic and Mechanistic Insight

被引:6
作者
Cazorla, Clement [1 ]
Billamboz, Muriel [2 ]
Chevrin-Villette, Carole [2 ]
Hapiot, Frederic [3 ]
Monflier, Eric [3 ]
Len, Christophe [1 ]
机构
[1] Univ Technol Compiegne, Sorbonne Univ, Ctr Rech Royallieu, CS 60319, F-60203 Compiegne, France
[2] Ecole Super Chim Organ & Minerale, 1 Allee Reseau Jean Marie Buckmaster, F-60200 Compiegne, France
[3] Univ Lille, CNRS, Cent Lille, ENSCL,UMR 8181,UCCS,Univ Artois, F-62300 Lens, France
关键词
dienes; green chemistry; mass spectrometry; microwave chemistry; palladium; TSUJI-TROST REACTION; PALLADIUM; WATER; ELECTROSPRAY; IONIZATION; SURFACTANT; CATALYST;
D O I
10.1002/cctc.201600343
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The first palladium-catalyzed bisallylic substitution on biobased bisallylic derivatives was explored. The developed method, performed under green conditions with microwave irradiation, led to valuable conjugated dienes. The mechanism was studied by ESI-MS and NMR spectroscopy, which highlighted the involvement of bis-p-allylpalladium complexes in the catalytic cycle.
引用
收藏
页码:2321 / 2328
页数:8
相关论文
共 35 条
[1]   Poisoning and deactivation of palladium catalysts [J].
Albers, P ;
Pietsch, J ;
Parker, SF .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 173 (1-2) :275-286
[2]   OBSERVATION OF CATALYTIC INTERMEDIATES IN THE SUZUKI REACTION BY ELECTROSPRAY MASS-SPECTROMETRY [J].
ALIPRANTIS, AO ;
CANARY, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6985-6986
[3]  
BARTON WRS, 2012, Patent No. 201261684878
[4]   Heterolytic splitting of allylic alcohols with palladium(0)-TPPTS in water.: Stabilities of the allylphosphonium salt of TPPTS and of the ionic complex [Pd(η3-allyl)(TPPTS)2]+ [J].
Basset, Jean-Marie ;
Bouchu, Denis ;
Godard, Gregory ;
Karame, Tyad ;
Kuntz, Emile ;
Lefebvre, Frederic ;
Legagneux, Nicolas ;
Lucas, Christine ;
Michelet, Daniel ;
Tommasino, Jean Bernard .
ORGANOMETALLICS, 2008, 27 (17) :4300-4309
[5]   First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies [J].
Billamboz, Muriel ;
Len, Christophe .
CHEMSUSCHEM, 2015, 8 (10) :1664-1675
[6]   Micellar Catalysis Using a Photochromic Surfactant: Application to the Pd-Catalyzed Tsuji-Trost Reaction in Water [J].
Billamboz, Muriel ;
Mangin, Floriane ;
Drillaud, Nicolas ;
Chevrin-Villette, Carole ;
Banaszak-Leonard, Estelle ;
Len, Christophe .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :493-500
[7]   Novel Strategy for the Bis-Butenolide Synthesis via Ring-Closing Metathesis [J].
Billamboz, Muriel ;
Legeay, Jean Christophe ;
Hapiot, Frederic ;
Monflier, Eric ;
Len, Christophe .
SYNTHESIS-STUTTGART, 2012, 44 (01) :137-143
[8]   Allylic substitution mediated by water and palladium:: Unusual role of a palladium(II) catalyst and ESI-MS analysis [J].
Chevrin, C ;
Le Bras, J ;
Hénin, F ;
Muzart, J ;
Pla-Quintana, A ;
Roglans, A ;
Pleixats, R .
ORGANOMETALLICS, 2004, 23 (20) :4796-4799
[9]   Water-mediated transition-metal-free Tsuji-Trost-type reaction [J].
Chevrin, C ;
Le Bras, J ;
Hénin, F ;
Muzart, J .
TETRAHEDRON LETTERS, 2003, 44 (44) :8099-8102
[10]  
Clavier H., 2012, ANGEW CHEM, V124, P8776