Metal-Ligand Cooperation in the Cycloisomerization of Alkynoic Acids with Indenediide Palladium Pincer Complexes

被引：62

作者：

Nebra, Noel

Monot, Julien

Shaw, Rosie

Martin-Vaca, Blanca ^{[1
]}

Bourissou, Didier

机构：

[1] Univ Toulouse, UPS, LHFA, F-31062 Toulouse, France

来源：

ACS CATALYSIS | 2013年 / 3卷 / 12期

关键词：

pincer complexes; metal-ligand cooperation; palladium; cycloisomerization; noninnocent ligand; homogeneous catalysis; CATALYZED CYCLIZATION; RUTHENIUM COMPLEXES; INTRAMOLECULAR CYCLIZATION; ASYMMETRIC CATALYSIS; CARBON-DIOXIDE; ENOL LACTONES; HYDROGEN; METHANOL; WATER; DEHYDROGENATION;

D O I：

10.1021/cs401029x

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：

Indenediide Pd complexes 1a-c are shown to very efficiently catalyze the cycloisomerization of alkynoic acids into alkylidene lactones via metal ligand cooperation (TON up to 2000). Complexes 1a-c are competent toward a broad range of alkynoic acids, including functionalized and internal ones, and give access to 5- as well as 6- and 7-membered lactones in excellent yields and with very high selectivities.

引用

页码：2930 / 2934

页数：5

共 53 条

[1] Anticancer platinum complexes as non-innocent compounds for catalysis in aqueous media
Aleman, Jose
del Solar, Virginia
Navarro-Ranninger, Carmen
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (03) : 454 - 456
[2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
Alonso, F
Beletskaya, IP
Yus, M
[J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
[3] Learning from the Neighbors: Improving Homogeneous Catalysts with Functional Ligands Motivated by Heterogeneous and Biocatalysis
Askevold, Bjorn
Roesky, Herbert W.
Schneider, Sven
[J]. CHEMCATCHEM, 2012, 4 (03) : 307 - 320
[4] Balaraman E, 2011, NAT CHEM, V3, P609, DOI [10.1038/NCHEM.1089, 10.1038/nchem.1089]
[5] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates
Bellina, F
Ciucci, D
Vergamini, P
Rossi, R
[J]. TETRAHEDRON, 2000, 56 (16) : 2533 - 2545
[6] TRANSITION-METAL-CATALYZED CYCLIZATION OF ALKYNOIC ACIDS TO ALKYLIDENE LACTONES
CHAN, DMT
MARDER, TB
MILSTEIN, D
TAYLOR, NJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) : 6385 - 6388
[7] Pd(II)-catalyzed cycloisomerisation of γ-alkynoic acids and one-pot tandem cycloisomerisation/CuAAC reactions in water
Garcia-Alvarez, Joaquin
Diez, Josefina
Vidal, Cristian
[J]. GREEN CHEMISTRY, 2012, 14 (11) : 3190 - 3196
[8] Acetylacetonato(phosphane)iridium Complexes: Synthesis and Catalytic Activity in the Cyclization of Alkynoic Acids
Geier, Michael J.
Vogels, Christopher M.
Decken, Andreas
Westcott, Stephen A.
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (29) : 4602 - 4610
[9] Coordination Versatility of sp3-Hybridized Pincer Ligands toward Ligand-Metal Cooperative Catalysis
Gelman, Dmitri
Musa, Sanaa
[J]. ACS CATALYSIS, 2012, 2 (12): : 2456 - 2466
[10] Cooperating ligands in catalysis
Griitzmacher, Hansjoerg
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1814 - 1818

← 1 2 3 4 5 6 →