Selective dimerization of arylalkynes to (E)-1,4-diaryl enynes catalyzed by the [Ru(p-cymene)Cl2]2/Acetic acid system under phosphine-free conditions

被引:54
作者
Bassetti, Mauro [1 ]
Pasquini, Chiara
Raneri, Antonino
Rosato, Deborah
机构
[1] Univ Roma La Sapienza, CNR, Ist Metodol Chim, Dipartimento Progettaz Mol, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
关键词
D O I
10.1021/jo0702692
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The commercially available di-mu-chlorobis[(p-cymene)chlororuthenium(II)] complex catalyzes the dimerization of aromatic alkynes in acetic acid at room temperature to form the corresponding (E)-1,4-diarylbut-1-ene-3-yne derivatives, with high stereoselectivity. The procedure does not require the use of additives and can be carried out in the presence of water or aprotic cosolvents, under homogeneous conditions.
引用
收藏
页码:4558 / 4561
页数:4
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共 54 条
[11]   Ruthenium-promoted Z-selective head-to-head dimerization of terminal alkynes in organic and aqueous media [J].
Chen, XG ;
Xue, P ;
Sung, HHY ;
Williams, ID ;
Peruzzini, M ;
Bianchini, C ;
Jia, GC .
ORGANOMETALLICS, 2005, 24 (18) :4330-4332
[12]   OLIGOPHOSPHANE LIGANDS .32. CATALYTIC DIMERIZATION OF 1-ALKYNES TO LINEAR 1-EN-3-YNES ON CIS-ARYLHYDRIDORUTHENIUM(II) CHELATE COMPLEXES - MOLECULAR-STRUCTURE OF (PP3)RUH(C6H4CF3-3) (PP3=P(CH2CH2CH2PME2)3) [J].
DAHLENBURG, L ;
FROSIN, KM ;
KERSTAN, S ;
WERNER, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 407 (01) :115-124
[13]   Chemo- and regioselective dimerization of terminal alkynes promoted by methylaluminoxane [J].
Dash, AK ;
Eisen, MS .
ORGANIC LETTERS, 2000, 2 (06) :737-740
[14]  
DYKER G, 2005, HDB C H TRANSFORMATI, V1, P62
[15]   PHENYLACETYLENE DIMERIZATION PROMOTED BY RUTHENIUM(II) COMPLEXES [J].
ECHAVARREN, AM ;
LOPEZ, J ;
SANTOS, A ;
MONTOYA, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 414 (03) :393-400
[16]   The dimerization and cyclotrimerization of acetylenes mediated by phosphine complexes of cobalt(I), rhodium(I), and iridium(I) [J].
Field, LD ;
Ward, AJ ;
Turner, P .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (11) :1085-1092
[17]   Ruthenium maltolato complexes [J].
Fryzuk, MD ;
Jonker, MJ ;
Rettig, SJ .
CHEMICAL COMMUNICATIONS, 1997, (04) :377-378
[18]   The reaction of ethynylferrocene with Cp*Rh half-sandwich complexes containing a chelating 1,2-dicarba-closo-dodecaborane(12)-1,2-dichalcogenolato ligand, Cp*Rh[E2C2(B10H10)], E = S, Se [J].
Herberhold, M ;
Yan, H ;
Milius, W ;
Wrackmeyer, B .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 623 (1-2) :149-152
[19]   CATALYTIC HEAD-TO-HEAD ALKYNE DIMERIZATION TO GIVE Z-ENYNES [J].
JUN, CH ;
LU, Z ;
CRABTREE, RH .
TETRAHEDRON LETTERS, 1992, 33 (47) :7119-7120
[20]   (Z)-selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes [J].
Katayama, H ;
Yari, H ;
Tanaka, M ;
Ozawa, F .
CHEMICAL COMMUNICATIONS, 2005, (34) :4336-4338