Article
Chemistry, Physical
Xing Ge, Xiuyu Fang, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A general and efficient protocol has been developed for the synthesis of acetamide-functionalized benzofurans using a palladium-catalyzed intramolecular cyclization and reductive aminocarbonylation reaction. The reaction proceeds in a single step, resulting in structure-defined benzofurans with acetamides as attractive functional groups. Various acetamide-functionalized benzofurans were obtained with moderate to good yields and good functional group compatibility using Mo(CO)6 as both CO source and reductant.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yang Yuan, Jiawang Liu, Xiao-Feng Wu
Summary: An unprecedented and challenging defluorinative carbonylation reaction was achieved with the first example of defluorinative carbonylative coupling established using a Pd/Cu cooperative catalyst system. This methodology, using gem-difluoroalkenes and aryl iodides as substrates, provides flexible and facile access to privileged alpha-fluorochalcones under mild reaction conditions in moderate-to-excellent yields. Mechanistic studies demonstrated that transmetalation between palladium and copper intermediates is a crucial step in the catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Yiwen Zhu, Zhengjie Le, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed double carbonylation reaction has been developed for the rapid construction of 4-oxo-4-(aryl/alkylamino)butanoic acid scaffolds, using benzene-1,3,5-triyl triformate (TFBen) as the CO surrogate. The reaction with aromatic and aliphatic primary amines proceeded well, yielding a variety of functionalized acids in high yields.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Zhengjie Le, Yiwen Zhu, Zhi-Peng Bao, Jun Ying, Xiao-Feng Wu
Summary: A new palladium-catalyzed reaction has been developed for the efficient synthesis of 1,5-dihydro-2H-pyrrol-2-ones using benzene-1,3,5-triyl triformate as the CO source.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A simple and selective method using carbon monoxide as a reducing agent was developed for the preparation of amides from nitroarenes and carboxylic acids. The protocol does not require non-gaseous additives, simplifying product isolation and saving reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A straightforward and selective method using carbon monoxide as a reductant was developed to prepare amides directly from nitroarenes and carboxylic acids. This protocol simplifies product isolation by not requiring any non-gaseous additives and preserves reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yan Shang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A new method has been developed for the construction of 1,5-dihydro-2H-pyrrol-2-one scaffolds through palladium-catalyzed carbonylative cyclization of propargyl amines and acid chlorides. The reaction provides a facile approach to access various 1-acyl-1,5-dihydro-2H-pyrrol-2-ones in high yields.
Article
Chemistry, Organic
Tingzhi Lin, Pengcheng Qian, Yan-En Wang, Mingjie Ou, Ning Cui, Yu Ye, Rui Hua, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: A direct and convenient method for the synthesis of aryl/alkenyl alkyl ketones has been developed. This method overcomes the limitations of previous methods and avoids the use of organometallic reagents.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Xiao-Feng Wu
Summary: This article develops an efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of 2-cyano-N-acetamide and 2-cyanoacetate compounds. The reaction proceeds under mild conditions via a radical intermediate, suitable for late-stage functionalization. Gram-scale experiment was successfully performed with low catalyst loading, yielding the target product excellently. Additionally, this transformation can be carried out under atmospheric pressure and provides alternative routes to drug precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yuya Hu, Rui Sang, Robby Vroemans, Guillaume Mollaert, Rauf Razzaq, Helfried Neumann, Henrik Junge, Robert Franke, Ralf Jackstell, Bert U. W. Maes, Matthias Beller
Summary: In this study, a straightforward and efficient method for the selective synthesis of diesters using palladium-catalyzed direct carbonylation of di- or polyols with readily available alkenes was presented. The use of a specific palladium catalyst with the built-in-base ligand L16 allowed for esterification of all alcohols and a high n/iso ratio. The synthesized diesters were evaluated as potential plasticizers in PVC films through the measurement of the glass transition temperature (T-g) using differential scanning calorimetry (DSC).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Linlin Ding, Yue Zhao, Hongjian Lu, Zhuangzhi Shi, Minyan Wang
Summary: For the first time, a catalytic enantioselective propargyl-aryl cross-coupling between two electrophiles was achieved in a stereoconvergent manner. The potential utility of this conversion is demonstrated in the facile construction of stereoenriched bioactive molecule derivatives and medicinal compounds based on the diversity of acetylenic chemistry. Detailed experimental studies have revealed the key mechanistic features of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Raffaella Mancuso, Ida Ziccarelli, Mariangela Novello, Corrado Cuocci, Roberto Centore, Nicola Della Ca', Diego Olivieri, Carla Carfagna, Bartolo Gabriele
Summary: The reactivity of 2-alkynylbenzoic acids under Pdl(2)/KI-catalyzed oxidative alkoxycarbonylation conditions has been studied. The reaction selectively produces high value added compounds under specific conditions. The structures of the products were confirmed by XRD analysis.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Yangyang Weng, Jingping Qu, Yifeng Chen
Summary: This study demonstrates the palladium-catalyzed allylic carbonylative Negishi cross-coupling reaction using sterically bulky aromatic isocyanides as a CO surrogate, leading to β,γ-unsaturated ketones with high regioselectivity and stereoselectivity. The advantages of this method include mild reaction conditions and a wide substrate scope due to the utilization of Negishi reagents as carbon nucleophiles.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Ben Niu, Yin Wei, Min Shi
Summary: In recent years, Pd-catalyzed annulation reactions using zwitterionic pi-allyl palladium intermediates have been extensively studied, demonstrating their importance in the synthesis of carbocyclic and heterocyclic compounds with potential pharmaceutical and biological applications. This review highlights the significant advances in organic synthesis based on zwitterionic pi-allyl palladium and propargyl palladium.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Jin-Bao Peng, Xin-Lian Liu, Lin Li, Xiao-Feng Wu
Summary: Carbonylation is a powerful method for the preparation of carbonylated compounds, and asymmetric carbonylation is a direct approach to constructing chiral compounds. This review summarizes recent achievements in palladium-catalyzed asymmetric carbonylation reactions.
SCIENCE CHINA-CHEMISTRY
(2022)
