Article
Chemistry, Organic
Wenlong Ren, Jinzi Huang, Yian Shi
Summary: An effective Pd-catalyzed regioselective hydroformylation process using N-formylsaccharin or 2,4,6-trichlorophenyl formate along with formic acid is described. Linear aldehydes can be obtained in high yield and with a high linear/branched ratio. The reaction is operationally simple without the need for external CO and H2.
Article
Chemistry, Multidisciplinary
Oleg L. Eliseev, Tatyana N. Bondarenko, Maria V. Tsapkina
Summary: A new protocol for Pd-catalyzed hydroxycarbonylation of olefins with formic acid under low pressure of CO has been developed. The reaction shows good selectivity towards 2-phenylpropionic acid in the carbonylation of styrene and linear acids in the carbonylation of terminal alkenes. The choice of catalyst precursor and solvent greatly affects the reaction.
MENDELEEV COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xia-Bin Xiang, Sheng Wang, Teng Xu, Shanshan Chen
Summary: An effective Pd-catalyzed regioselective hydroesterification of 1,3-conjugated enynes with aryl formates was found, achieving selective formation of 2-ester-substituted 1,3-dienes in good yields with excellent regioselectivities using the Pd-CyDPEphos catalytic system.
Article
Chemistry, Organic
Wenlong Ren, Mingzhou Wang, Jianqiong Guo, Jintao Zhou, Jianxiao Chu, Yuan Shi, Yian Shi
Summary: A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can be obtained easily under mild reaction conditions with high regioselectivities. The operation of the reaction is simple and does not require handling toxic CO. The ligand and LiCl play important roles in reaction reactivity and selectivity.
Article
Chemistry, Physical
Tong Liu, Zongji Zhang, Ling Yan, Zhibin Zhang, Yi Zhang, Yansheng Yin
Summary: A simple wet chemical method was used to prepare two-dimensional transition metal carbides (MXene), and Pd metal nanoparticles were loaded on its surface to catalyze the dehydrogenation of formic acid. The prepared Pd/PDA-MXene catalyst exhibited excellent catalytic activity in formic acid decomposition process, and maintained stable activity in five consecutive catalytic cycles.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2021)
Article
Chemistry, Organic
Young Ho Kim, Dong Bin Kim, Su San Jang, So Won Youn
Summary: A Pd-catalyzed intramolecular allylic C-H amination method has been developed, allowing for the synthesis of diverse 1,3-X,N-heterocycles through selective allylic C-H cleavage and pi-allylpalladium formation. The use of substrates containing a labile allylic moiety and new catalytic systems overcomes significant challenges for achieving highly chemo- and regioselective allylic C-H amination.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shu-Mei Xia, Zhi-Wen Yang, Xiang-Yang Yao, Kai-Hong Chen, Li-Qi Qiu, Liang-Nian He
Summary: An unprecedented strategy has been developed for the Cu-catalyzed hydrocarboxylation of alkynes with HCOOH to yield (E)-acrylic derivatives with high regio- and stereoselectivity, utilizing ppm levels of a Pd catalyst for synergistic effects. This method demonstrates successful hydrocarboxylation of both symmetrical and unsymmetrical alkynes bearing various functional groups. Mechanistic investigations suggest a cooperative catalysis mechanism involving Cu and ppm Pd, with HCOOH serving as a hydrogen source.
Article
Chemistry, Organic
Vladimir I. Kurganskiy, Roman Ottenbacher, Mikhail Shashkov, Evgenii P. Talsi, Denis G. Samsonenko, Konstantin P. Bryliakov
Summary: In this paper, the direct selective C-H lactonization of fatty acids (C5-C16) catalyzed by manganese(II) complexes bearing bis-amino-bis-pyridine ligands was reported. The catalyst system used environmentally benign hydrogen peroxide as an oxidant and showed high efficiency, providing gamma-lactones in 60-90% yields under optimized conditions. Remarkably, by changing the reaction conditions, the oxidation of hexanoic acid could be diverted to the formation of delta-caprolactone in up to 67% yield. Furthermore, the possibility of obtaining (omega-1)-hydroxy derivatives from linear C7-C10 acids in up to 48% yields was demonstrated.
Article
Chemistry, Organic
Laszlo Kollar, Attila Takacs, Csilla Molnar, Andrew Kovacs, Laszlo T. Mika, Peter Pongracz
Summary: In this study, palladium-catalyzed amino- and alkoxycarbonylation reactions of aryl iodides were investigated using aliphatic heterobifunctional N,O-nucleophiles. Selective synthesis of amide alcohols and amide esters was achieved by adjusting the base and substrate ratio. The effect of iodobenzene substituents on product selectivity was studied and yielded surprising results. Various heteroaromatic substrates and related nucleophiles were tested under optimized conditions, resulting in moderate to good yields of the target compounds. The reactions of serinol and 1,3-diamino-2-propanol as model trifunctional compounds showed high chemoselectivity towards amide ester products. A rational catalytic cycle was proposed based on the coordinative properties of the applied nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hui-Yi Yang, Ya-Hong Yao, Ming Chen, Zhi-Hui Ren, Zheng-Hui Guan
Summary: The Pd-catalyzed Markovnikov hydroaminocarbonylation of alkenes provides a straightforward and efficient method for the synthesis of amides bearing an a quaternary carbon. The reaction proceeds through a palladium hydride pathway, with hydropalladation and CO insertion being reversible steps and aminolysis as the likely rate-limiting step.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Xia-Bin Xiang, Sheng Wang, Teng Xu, Shanshan Chen
Summary: We developed an effective Pd-catalyzed regioselective hydroesterification method for 1,3-conjugated enynes with aryl formates. Using the Pd-CyDPEphos catalytic system, the conjugated enynes reacted with phenyl formates to selectively provide 2-ester-substituted 1,3-dienes in good yields and excellent regioselectivities.
Article
Chemistry, Organic
Andrea Zanetti, Geoffrey Schwertz, Marllon Nascimento de Oliveira, Mario Andres Gomez Fernandez, Zacharias Amara, Janine Cossy
Summary: A regioselective Pd-catalyzed allylic oxidation of amorphadiene, a key precursor to artemisinin, is described, which can substitute P450 enzymes in artemisinin biosynthesis and enhance the value of waste in the industrial semisynthetic process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jiaqi Yuan, Xiaofei Zhang, Chunhao Yang
Summary: The study presents a new method for the direct alkylation of the C-H bond at the alpha-position of furans catalyzed by palladium catalyst, yielding a variety of alpha-alkylfurans in moderate to good yields. This method has high substrate tolerance and shows promising utility in medicinal chemistry.
Article
Chemistry, Organic
Ming-Chen Fu, Jia-Xin Wang, Wei Ge, Fang-Ming Du, Yao Fu
Summary: In this study, we present an efficient and practical method for the dehalocarboxylation of C(sp(2))-halides using formate and a CO2 radical anion in a nickel-mediated bond-forming process. Various aryl iodides, aryl bromides, and alkenyl bromides with different functional groups successfully underwent the reaction through visible-light photoredox nickel dual catalysis. The synthesis of C-13-labeled drug intermediates and gram-scale synthesis of commercial drugs demonstrated the synthetic value of this approach in drug discovery.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Yang Yuan, Fengqian Zhao, Xiao-Feng Wu
Summary: This study introduces a copper-catalyzed enantioselective hydroaminocarbonylation method for constructing alpha-chiral secondary amides. The method shows high yields and high levels of enantioselectivity under very mild conditions. Additionally, alpha,beta-Unsaturated secondary amides can be produced by using alkynes as the substrate.
Article
Chemistry, Organic
Wenju Chang, Jingfu Li, Wenlong Ren, Yian Shi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Jingfu Li, Wenju Chang, Wenlong Ren, Jie Dai, Yian Shi
Article
Chemistry, Organic
Wenju Chang, Jie Dai, Jingfu Li, Yuan Shi, Wenlong Ren, Yian Shi
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Organic
Wenlong Ren, Jianxiao Chu, Fei Sun, Yian Shi
Article
Chemistry, Organic
Wenlong Ren, Fei Sun, Jianxiao Chu, Yian Shi
Article
Chemistry, Multidisciplinary
Ping Zhang, Wenju Chang, Hongyun Jiao, Yanshang Kang, Wenxuan Zhao, Peipei Cui, Yong Liang, Wei-Yin Sun, Yi Lu
Summary: The study established a successful electron-deficient catalyzed annulation of N-pentafluorophenylbenzamides with internal alkynes, aided by Lewis acid silver salt, exhibiting a broad tolerance for different substituents on aromatic rings or alkyl-substituted alkynes in the catalytic system.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Ping Zhang, Wenju Chang, Yan-Shang Kang, Wenxuan Zhao, Pei-Pei Cui, Yong Liang, Wei-Yin Sun, Yi Lu
Article
Chemistry, Organic
Jianhui Qiao, Wenju Chang, Wenxuan Zhao, Yong Liang, Shaozhong Wang
Summary: A kinetic resolution method has been developed for racemic spiroindolines with s factors <= 15200, allowing the access to enantiomerically enriched indoleannulated medium-sized lactams and spiroindolines through Ir-catalyzed asymmetric allylative ring-opening reaction. Density functional theory calculations support the accurate discrimination of two spiroindoline enantiomers by (eta(3)-allyl)-iridium(III) species and ensure the stereoselective formation of two contiguous stereogenic centers and one axis in the medium-sized lactams.
Article
Chemistry, Multidisciplinary
Zhenghui Kang, Wenju Chang, Xue Tian, Xiang Fu, Wenxuan Zhao, Xinfang Xu, Yong Liang, Wenhao Hu
Summary: The study presents a novel asymmetric allylation reaction through ternary cooperative catalysis, enabling the expedient access to chiral alpha,alpha-disubstituted ketones with high enantioselectivity. Experimental and computational studies have elucidated the mechanism and origin of enantioselectivity in this three-component reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wenju Chang, Yu Chen, Shuo Lu, Hongyun Jiao, Yajun Wang, Tianyu Zheng, Zhuangzhi Shi, Yingbin Han, Yi Lu, Yi Wang, Yi Pan, Jin-Quan Yu, Kendall N. Houk, Fang Liu, Yong Liang
Summary: This study reports the design of catalysts that can selectively control the tunable borylation of various arenes through the use of directed ligands. By introducing different directing groups, the catalysts are able to precisely control the functionalization of the meta or para position in the arene.
Article
Chemistry, Multidisciplinary
Yajun Wang, Wenju Chang, Shengmeng Qin, Han Ang, Jiawei Ma, Shuo Lu, Yong Liang
Summary: Herein, we report a tunable meta- and para-selective C-H borylation of aryl sulfonyl compounds enabled by computationally designed ligands and iridium catalyst. This method is capable of accommodating a broad range of substrates under mild reaction conditions and can achieve gram-scale preparation with low iridium catalyst loading. Our method provides a general solution to installing functional groups at either meta- or para-position of aryl sulfones and aryl sulfonamides with good to excellent selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Sifan Yu, Wenju Chang, Ruyu Hua, Xiaoting Jie, Mengchu Zhang, Wenxuan Zhao, Jinzhou Chen, Dan Zhang, Huang Qiu, Yong Liang, Wenhao Hu
Summary: This article reports various highly diastereoselective and enantioselective four-component reactions. The trapping strategy used in this work allows for the generation of a wide range of reaction products under mild conditions, showing high functional group tolerance. The proposed mechanism of this multicomponent reaction is also discussed.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Weipeng Li, Yu Chen, Yinghan Chen, Siyu Xia, Wenju Chang, Chengjian Zhu, K. N. Houk, Yong Liang, Jin Xie
Summary: The combination of gold catalysis and silver salt enables selective arylation of amides in unprotected polypeptides, resulting in N-aryl amide peptides with various functional motifs. This method exhibits excellent biocompatibility and has been applied to functionalize peptide drugs and complex peptides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
