Transfer semihydrogenation of alkynes catalyzed by a zero-valent palladium N-heterocyclic carbene complex

被引：156

作者：

Hauwert, Peter ^{[1
]}

Maestri, Giovanni ^{[2
]}

Sprengers, Jeroen W. ^{[1
]}

Catellani, Marta ^{[2
]}

Elsevier, Cornelis J. ^{[1
]}

机构：

[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WV Amsterdam, Netherlands

[2] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 17期

关键词：

alkynes; carbene ligands; hydrogen transfer; hydrogenation; palladium;

D O I：

10.1002/anie.200705638

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Beyond Lindlar and without hydrogen: Transfer hydrogenation of internal alkynes catalyzed by a palladium(0) catalyst containing an N-heterocyclic carbene ligand gives Z alkenes without over-reduction to alkanes (see scheme). Contrary to most transfer hydrogenations, ketones are not reduced. As such, this is the first catalyst that shows excellent stereo- and chemo-selectivity for the semihydrogenation of alkynes without the need for hydrogen gas. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3223 / 3226

页数：4

共 50 条

[41] A cooperative N-heterocyclic carbene/palladium catalysis system
Liu, Kun
Hovey, M. Todd
Scheidt, Karl A.
CHEMICAL SCIENCE, 2014, 5 (10) : 4026 - 4031
[42] Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Aldehyde Acylation of Allylic Amines
Ohnishi, Nagisa
Yasuda, Shigeo
Nagao, Kazunori
Ohmiya, Hirohisa
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (07) : 1133 - 1135
[43] Polycondensation of haloarylketones catalyzed by palladium compounds bearing N-heterocyclic carbene (NHC) ligands
Matsubara, Kouki
Okazaki, Hiromi
Senju, Misako
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (17) : 3693 - 3699
[44] Transfer Semihydrogenation of Alkynes Catalyzed by Imidazo[1,5-a]pyrid-3-ylidene-Pd Complexes: Positive Effects of Electronic and Steric Features on N-Heterocyclic Carbene Ligands
Shibahara, Fumitoshi
Mizuno, Takahiro
Shibata, Yoshifuru
Murai, Toshiaki
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2020, 93 (03) : 332 - 337
[45] Pyridine functionalised N-heterocyclic carbene complexes of palladium
Tulloch, AAD
Danopoulos, AA
Tooze, RP
Cafferkey, SM
Kleinhenz, S
Hursthouse, MB
CHEMICAL COMMUNICATIONS, 2000, (14) : 1247 - 1248
[46] N-Heterocyclic Carbene Catalyzed γ-Dihalomethylenation of Enals by Single-Electron Transfer
Yang, Wen
Hu, Weimin
Dong, Xiuqin
Li, Xin
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (51) : 15783 - 15786
[47] Development of N-Heterocyclic Carbene (NHC)-palladium Complex Catalyst and Immobilized NHC-palladium Complex Catalyst
Mizusaki, Tomoteru
JOURNAL OF THE JAPAN PETROLEUM INSTITUTE, 2023, 66 (01) : 1 - 7
[48] Kinetics and Mechanism of Allene Racemization Catalyzed by a Gold N-Heterocyclic Carbene Complex
Li, Hao
Harris, Robert J.
Nakafuku, Kohki
Widenhoefer, Ross A.
ORGANOMETALLICS, 2016, 35 (13) : 2242 - 2248
[49] Hydrogenation of hexene catalyzed by a ruthenium (II) complex with N-heterocyclic carbene ligands
Achour, Sofiene
Hosni, Zied
Tangour, Bahoueddine
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2024, 124 (15)
[50] Isolation of an N-Heterocyclic Carbene Complex of a Borasilene
Franz, Daniel
Szilvasi, Tibor
Poethig, Alexander
Inoue, Shigeyoshi
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (47) : 11036 - 11041

← 1 2 3 4 5 →