Markovnikov-Selective Palladium Catalyst for Carbonylation of Alkynes with Heteroarenes

被引：32

作者：

Liu, Jie ^{[1
]}

Li, Haoquan ^{[1
]}

Duehren, Ricarda ^{[1
]}

Liu, Jiawang ^{[1
]}

Spannenberg, Anke ^{[1
]}

Franke, Robert ^{[2
,3
]}

Jackstell, Ralf ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

[2] Evonik Performance Mat GmbH, Paul Baumann Str 1, D-45772 Marl, Germany

[3] Ruhr Univ Bochum, Lehrstuhl Theoret Chem, D-44780 Bochum, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 39期

关键词：

alkynes; carbonylation; Pligands; palladium; regioselectivity; DEACTIVATED ARYL CHLORIDES; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; BITE ANGLE; REGIOSELECTIVE SYNTHESIS; HOMOGENEOUS CATALYSIS; PHOSPHINE-LIGANDS; CARBON-MONOXIDE; BOND FORMATION; EFFICIENT;

D O I：

10.1002/anie.201706794

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new class of palladium catalysts, based on heterocyclic diphosphines, was rationally designed and synthesized. Application of one of these catalysts allows novel Markovnikov-selective carbonylation of non-activated alkynes with heteroarenes to give the corresponding branched ,alpha,beta-unsaturated ketones in excellent yields (up to 97%) and regioselectivities (b/l up to 99:1). In addition to heteroarenes, other common nucloephiles (alcohol, phenol, amine, and amide) furnish the desired carbonylation products smoothly in high yields.

引用

页码：11976 / 11980

页数：5

共 50 条

[41] The Mechanism of Markovnikov-Selective Epoxide Hydrogenolysis Catalyzed by Ruthenium PNN and PNP Pincer Complexes
Head, Marianna C.
Joseph, Benjamin T.
Keith, Jason M.
Chianese, Anthony R.
ORGANOMETALLICS, 2023, 42 (05) : 347 - 356
[42] An efficient Au(I) catalyst for double hydroarylation of alkynes with heteroarenes
Luo, Cuicui
Yang, Hongwei
Mao, Rongfang
Lu, Chunxu
Cheng, Guangbin
NEW JOURNAL OF CHEMISTRY, 2015, 39 (05) : 3417 - 3423
[43] Palladium sulphide - A highly selective catalyst for the gas phase hydrogenation of alkynes to alkenes
McCue, Alan J.
Guerrero-Ruiz, Antonio
Rodriguez-Ramos, Inmaculada
Anderson, James A.
JOURNAL OF CATALYSIS, 2016, 340 : 10 - 16
[44] Palladium/phosphaadamantane catalyst enables an exclusively trans-selective chlorocarbamoylation of alkynes
Le, Christine
Hou, Xiao
Sperger, Theresa
Schoenebeck, Franziska
Lautens, Mark
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[45] An Exclusively trans-Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst
Le, Christine M.
Hou, Xiao
Sperger, Theresa
Schoenebeck, Franziska
Lautens, Mark
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (52) : 15897 - 15900
[46] Selective Synthesis of Secondary Alkylboronates: Markovnikov-Selective Hydroboration of Vinylarenes with Bis(pinacolato)diboron Catalyzed by a Nickel Pincer Complex
Hashimoto, Toru
Shiota, Keisuke
Yamaguchi, Yoshitaka
ORGANIC LETTERS, 2020, 22 (10) : 4033 - 4037
[47] Directing-Group-Assisted Markovnikov-Selective Hydrothiolation of Styrenes with Thiols by Photoredox/Cobalt Catalysis
Xiao, Qian
Zhang, Hong
Li, Jing-Hong
Jian, Jing-Xin
Tong, Qing-Xiao
Zhong, Jian-Ji
ORGANIC LETTERS, 2021, 23 (09) : 3604 - 3609
[48] Heterogenizing palladium tetraiodide catalyst for carbonylation reactions
Ziccarelli, Ida
Mancuso, Raffaella
Giacalone, Francesco
Calabrese, Carla
La Parola, Valeria
De Salvo, Alex
Della Ca', Nicola
Gruttadauria, Michelangelo
Gabriele, Bartolo
JOURNAL OF CATALYSIS, 2022, 413 : 1098 - 1110
[49] Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes
Ma, Haojie
Ren, Xiaoyu
Zhou, Xiaoqiang
Ma, Chaowei
He, Yongqin
Huang, GuoSheng
TETRAHEDRON LETTERS, 2015, 56 (44) : 6022 - 6029
[50] Development of an Improved Rhodium Catalyst for Z-Selective Anti-Markovnikov Addition of Carboxylic Acids to Terminal Alkynes
Wei, Siping
Pedroni, Julia
Meissner, Antje
Lumbroso, Alexandre
Drexler, Hans-Joachim
Heller, Detlef
Breit, Bernhard
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (36) : 12067 - 12076

← 1 2 3 4 5 →