Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wei Huang, Jiahui Bai, Yinlong Guo, Qinglei Chong, Fanke Meng
Summary: A catalytic enantioselective coupling of 1,1-disubstituted allenes and aldehydes is achieved through regiodivergent oxidative cyclization followed by stereoselective protonation or reductive elimination promoted by chiral phosphine-Co complexes. This unprecedented reaction pathway for Co catalysis allows for the catalytic enantioselective generation of metallacycles with divergent regioselectivity accurately controlled by chiral ligands, leading to a wide range of allylic alcohols and homoallylic alcohols in high yields and excellent regioselectivity, diastereoselectivity, and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yuwei Zong, Qiao Ma, Gavin Chit Tsui
Summary: In this study, a nucleophilic vinylic substitution reaction was developed to efficiently synthesize trisubstituted alkenes with stereocontrol under simple conditions. Additionally, dimerization of monofluoroalkenes to form (E,E)-divinyl ethers was observed, triggered by adventitious water in the reaction mixture.
Article
Chemistry, Applied
Yuki Umakoshi, Yusuke Takemoto, Akira Tsubouchi, Viktor V. Zhdankin, Akira Yoshimura, Akio Saito
Summary: A transition metal iodine catalyst is used to synthesize oxazoles through C-C bond formation between unfunctionalized alkynes and arenes, resulting in the introduction of aryl groups into the side chain of the compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Nadia Ledermann, Alae-Eddine Moubsit, Thomas J. J. Mueller
Summary: A library of 19 differently substituted 3-iodoindoles has been generated by a consecutive four-component reaction, which provides a concise one-pot synthesis of valuable substrates for Suzuki arylations. Some of the synthesized compounds exhibit good reaction activity and emission properties in the Suzuki arylations.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Fengxi Li, Chunyu Wang, Yaning Xu, Zixian Zhao, Jiali Su, Chenhan Luo, Yujie Ning, Zhengqiang Li, Chen Li, Lei Wang
Summary: The research introduces a green and efficient method for the synthesis of unsymmetrical trisubstituted 1,3,5-triazines from isothiocyanate, amidines, and 1,1,3,3-tetramethylguanidine, achieving high yields under optimal conditions with Hemoglobin from rabbit blood as the catalyst. This enzymatic approach demonstrates the potential for extending the application of enzyme catalytic promiscuity in organic synthesis.
MOLECULAR CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Meng-Yao Li, Shuyang Zhai, Xiao-Mei Nong, Ao Gu, Jiatong Li, Guo-Qiang Lin, Yingbin Liu
Summary: In recent years, the synthesis and application of alkenes, particularly triphenylethenes (TriPEs), have gained attention due to their lower molecular torsion and balanced conjugation, resulting in the aggregation-induced emission (AIE) effect. The geometry of double bonds significantly affects luminescence, making it important to provide a comprehensive summary of stereoselective synthetic strategies for trisubstituted alkenes. This review outlines common strategies for stereoselective synthesis, discussing the origin of stereoselectivity and the types of substrates, while also exploring the AIE properties of TriPE and its versatile applications in optoelectronic devices, stimuli-responsive materials, sensors, and therapies.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Rimpa De, Avantika Hasija, Deepak Chopra, Mrinal K. Bera
Summary: A practical and efficient method for the construction of poly substituted oxazoles was developed using a catalytic amount of potassium iodide and TBHP as the green oxidant via amidation followed by intramolecular oxidative cyclization of enaminone derivatives under mild reaction conditions. The attractive feature of this method is the simultaneous oxidation of benzylic CeH bond and dehydrogenation of enaminone in one pot under base free conditions.
Article
Chemistry, Multidisciplinary
Yongliang Zhang, Ke Zhao, Xinyi Li, Carlos D. Quintanilla, Liming Zhang
Summary: By using a chiral bifunctional phosphine ligand, a highly efficient and enantioselective dearomatization of phenols is achieved through metal-ligand cooperation. The reaction shows great generality by allowing substitutions at various positions of benzene, including electron-withdrawing groups and carbon-based groups. Spirocyclohexadienone-pyrrol-2-ones, spirocyclohexadienone-butenolides, and spirocyclohexadenone-cyclopentenones are formed in high yields and with high enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ke Zhao, Philip Kohnke, Ziguang Yang, Xinpeng Cheng, Shu-Li You, Liming Zhang
Summary: A gold(I)-catalyzed enantioselective dearomatization is achieved through metal-chiral ligand cooperation. A new and divergent synthesis of chiral bifunctional binaphthyl-2-ylphosphines is developed for rapid access to these ligands, enabling broad substrate scope. The selective acceleration of one enantiomer formation is achieved through hydrogen bonding between substrate and ligand remote basic group, leading to enantiomeric excesses up to 98%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Tamal Ballav, Rajesh Chakrabortty, Aniruddha Das, Suman Ghosh, Venkataraman Ganesh
Summary: This review summarizes the research achievements in the field of synergistic dual catalysis in recent years, highlighting the unique strategies of carbon-carbon and carbon-heteroatom bond formation achieved by combining Pd catalyst with transition metals, Lewis acids, or organocatalysts. The wide applications of these strategies in pharmaceutical and agrochemical industries are also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Subba Rao Polimera, Andivelu Ilangovan, Murugaiah A. M. Subbaiah
Summary: This study discovered that silyl enol ethers can be used as a masked source of saturated ketones to produce beta-aryl enones and their derivatives through dehydrosilylation and subsequent oxidative arylation using Pd-(II) catalysis. Oxygen was found to be an efficient and environmentally friendly oxidant for both dehydrosilylation and arylation. The arylation conditions can be customized to utilize aryl halides as an alternative source of arylation agents. 35 examples were tested with up to 95% yield, and mechanistic studies revealed a cationic Pd-(II)-based catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yujuan Xie, Liliang Huang, Huihui Feng, Yayu Qi, Erik V. Van der Eycken, Huangdi Feng
Summary: An efficient strategy for the synthesis of multisubstituted pyridines via oxidative alkynylation, radical addition, and intramolecular cycloaddition is presented. This method offers high selectivity, good economic efficiency, and broad applicability.
Article
Chemistry, Organic
Subba Rao Polimera, Andivelu Ilangovan, Murugaiah A. M. Subbaiah
Summary: Silyl enol ethers were used as a masked source of saturated ketones for the synthesis of β-aryl enones and their derivatives. Through dehydrosilylation and oxidative arylation using arylboronic acids, these compounds were generated in situ using a one-pot relayed Pd-(II) catalysis under base-free conditions. Oxygen was found to be an effective oxidant for both dehydrosilylation and arylation reactions. The arylation conditions could be customized to utilize aryl halides as an alternative source of arylating agents. The study investigated the preparative scope using 35 examples with yields up to 95%, and mechanistic studies suggested a cationic Pd-(II)-based catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Xiaoyu Yang
Summary: Helicenes and helicene-like molecules with unique helical chirality have found wide applications in various research fields. However, the catalytic enantioselective synthesis of helicenes has been relatively underexplored. In the past two decades, significant progress has been made in this field, including methods enabled by both transition metal catalysis and organocatalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
