Palladium-Catalyzed Dehydrogenative Carbonylative Esterification of Allenoic Acids for the Synthesis of γ-Butyrolactone Derivatives

被引：2

作者：

Wang, Bolin ^{[1
]}

Ren, Mingzhe ^{[1
]}

Iqbal, Nasir ^{[1
]}

Mu, Xin ^{[1
]}

Backvall, Jan-E. ^{[2
]}

Yang, Bin ^{[1
]}

机构：

[1] Xi An Jiao Tong Univ, Sch Chem, Xian 710049, Peoples R China

[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 12期

基金：

中国国家自然科学基金; 瑞典研究理事会;

关键词：

COUPLING REACTIONS; TERMINAL ALLENES; CARBON-MONOXIDE; ARYLATION; MIGRATION;

D O I：

10.1021/acs.orglett.4c00572

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient dehydrogenative carbonylative esterification of allenoic acids using Pd-catalysis was developed, providing a novel approach to synthesizing esterified gamma-butyrolactone derivatives with consistently good to excellent results demonstrated across over 50 examples. Additionally, we used a heterogeneous catalyst known as Pd-AmP-MCF and harnessed biomimetic-aerobic-oxidation conditions to facilitate the practical execution of this reaction. Furthermore, our detailed study of gamma-butyrolactone products highlighted their potential in synthesizing bioactive compounds.

引用

页码：2430 / 2434

页数：5

共 50 条

[41] Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkynes: Efficient Construction of α-Chirality of Ketones
Yang, Bin
Qiu, Youai
Jiang, Tuo
Wulff, William D.
Yin, Xiaopeng
Zhu, Can
Backvall, Jan-E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) : 4535 - 4539
[42] Palladium-Catalyzed Oxidative Carbonylative Coupling Reactions of Arylboronic Acids with Styrenes to Chalcones under Mild Aerobic Conditions
Wu, Xiao-Feng
Neumann, Helfried
Beller, Matthias
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (02) : 282 - 285
[43] Biaryl Diketone Synthesis via Palladium-catalyzed Carbonylative Coupling with Carbon Monoxide or Various Metal Carbonyls
Cho, Soo Kyung
Song, Ju Hyun
Hahn, Jung Tae
Jung, Dai Il
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (10) : 1567 - 1570
[44] Palladium-Catalyzed Decarboxylative Arylation of Benzoylacrylic Acids toward the Synthesis of Chalcones
Unoh, Yuto
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) : 5096 - 5102
[45] Palladium-catalyzed B-Diarylation of Diethylaminoborane for the Synthesis of Diarylborinic Acids
Shimazumi, Ryoma
Igarashi, Takuya
Tobisu, Mamoru
CHEMISTRY LETTERS, 2020, 49 (07) : 760 - 763
[46] Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation
Chniti, Sami
Kollar, Laszlo
Benyei, Attila
Takacs, Attila
MOLECULES, 2022, 27 (01):
[47] Palladium-Catalyzed Dehydrogenative β′-Functionalization of β-Keto Esters with Indoles at Room Temperature
Leskinen, Mikko V.
Yip, Kai-Tai
Valkonen, Arto
Pihko, Petri M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) : 5750 - 5753
[48] Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives
Zhi, Wubin
Li, Jingya
Zou, Dapeng
Wu, Yusheng
Wu, Yangjie
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12286 - 12293
[49] Palladium-Catalyzed Carbonylative Cyclization of β-Bromo-α,β-Unsaturated Ketones Leading to Alkylidenefuranones
Chan Sik Cho
Hyo Bo Kim
Catalysis Letters, 2010, 140 : 116 - 120
[50] Palladium-Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones
Zhou, Xibing
Ding, Yongzheng
Huang, Hanmin
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (11) : 1678 - 1682

← 1 2 3 4 5 →