Article
Chemistry, Multidisciplinary
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Summary: The Rh-catalyzed reaction allows for the efficient synthesis of cis-fused bicyclic products with excellent selectivity and tolerance towards synthetically useful functional groups. The proposed mechanism involves the rapid racemization of the allene moiety in the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ying-Ying Liu, Shao-Han Sun, Xiang-Ting Min, Boshun Wan, Qing-An Chen
Summary: Phthalimide derivatives, commonly found in biologically important molecules, have attracted considerable attention for their potential applications in drug development, fungicides, and anticancer agents. This review focuses on recent advances in catalytic strategies for directly modifying the phthalimide moiety, including decarbonylation and derivatization reactions. Various decarbonylative addition reactions, polymerization, alkylation, arylation, and protodecarbonylation reactions have been demonstrated. The review also discusses the mechanisms involved and highlights the importance of further developments in this field.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
C. Rose Kennedy, Matthew Joannou, Janelle E. Steves, Jordan M. Hoyt, Carli B. Kovel, Paul J. Chirik
Summary: This study describes the selective intermolecular homodimerization and cross-cycloaddition of vinylsilanes with unbiased 1,3-dienes catalyzed by a pyridine-2,6-diimine (PDI) iron complex. The chemoselectivity of these reactions was found to be distinct from that of similar alpha-olefin reactions with 1,3-dienes. Mechanistic studies provided insights into substrate-controlled regioselectivity, and identified diamagnetic iron diene and paramagnetic iron olefin complexes as catalyst resting states. The relative rates of beta-H elimination and C-C reductive elimination were ultimately governed by the silyl substituents, dictating final product formation.
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Organic
Lorand Kiss, Jorge Escorihuela
Summary: Density functional theory calculations were used to investigate the reactivity and regioselectivity of 1,3-dipolar cycloaddition reactions. The calculated activation free energies reproduced the experimentally observed product ratios. Both electronic and steric effects influenced the regioselectivities.
Article
Chemistry, Organic
Hong-Jing Long, Lei Zhang, Bing Lian, De-Cai Fang
Summary: This study investigated the ruthenium-catalyzed decarbonylative annulation of an alkyne with a hydroxychromone, revealing key steps such as the breaking of C-C bonds and the favorable reaction pathways. The calculations also utilized the steady-state approximation and modified energy span model to determine the apparent activation free energy of the catalytic cycle.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Gautam Kumar, Zheng-Wang Qu, Stefan Grimme, Indranil Chatterjee
Summary: Catalytic hydroarylation reactions of conjugated dienes using tris(pentafluorophenyl)borane as a Lewis acid catalyst show a broad substrate scope for highly regioselective functionalization of sterically hindered aniline derivatives. Experimental and theoretical studies reveal the crucial role of residual water and B(C6F5)(3) complex in the reaction mechanism.
Article
Chemistry, Organic
Rayees Ahmad Naikoo, Rashmi Sharma, Rupesh Kumar, Gaurav Bhargava
Summary: The manuscript presents a synthetic method for the formation of 5-(methylisoindole-1,3-dione) pyrimidinones. It involves the [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with 2-(3-Oxo-allyl)-isoindole-1,3-dione generated in situ. The synthesized pyrimidinones have significant pharmaceutical profiles and can serve as valuable organic synthons. Mechanistic insights are also proposed.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jie Huang, Ling-Ling Chen, Tong-Mei Ding, Zhi-Min Chen
Summary: An efficient iron-catalyzed hydroarylation of 1,3-dienes with indoles has been developed for the first time. This protocol utilizes the green and inexpensive Earth-abundant metal iron as the catalyst. The reaction features convenience, mild conditions, and high atom utilization efficiency, allowing for the synthesis of various molecules containing alkenyl and indole groups.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ying Li, Wei-Song Zhang, Shao-Han Sun, Yong-Kang Mei, Ding-Wei Ji, Yan-Cheng Hu, Qing-An Chen
Summary: Leveraging the power of organometallic chemistry, this study presents a regiodivergent hydrobivinylation of enones with dienes catalyzed by nickel(0). Aryldienes efficiently participate in the reaction, providing 1,4-disubstituted dienes with good regio- and stereoselectivity, while the addition site shifts to the C1 position in the case of alkyldienes. The preferential formation of oxanickelacycle is crucial for the success of this strategy. Furthermore, the resulting diene products can undergo a variety of complex transformations, highlighting the potential of this protocol.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Qiao-Juan Jiang, Yu-Tao Min, Yan-Ping Liu, Hua Li, Jun-Ao Peng, Cong-Jun Liu
Summary: An efficient Ir(iii)-catalyzed decarbonylative annulation of salicylaldehydes with cyclohexane-1,3-diones has been achieved via the in situ generated iodonium ylides. The reaction proceeds smoothly under mild and operationally simple conditions, affording a variety of benzofuran derivatives in moderate to high yields with good functional group tolerance. Moreover, the large-scale synthesis and further modification of the products highlight the utility of this protocol.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Yu-Yang Zhang, Han Li, Xiaoding Jiang, Chitreddy V. Subba Reddy, Hao Liang, Yaqi Zhang, Rihui Cao, Raymond Wai-Yin Sun, Man Kin Tse, Liqin Qiu
Summary: A new synthetic method was developed for the synthesis of functional flavones using nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes, with yields ranging from 65% to 99%. Terminal alkynes with substituted phenyl groups and internal alkynes like aryl acyl acetylenes and diphenylacetylenes are suitable substrates for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Arthur Flaget, Cheng Zhang, Clement Mazet
Summary: Ni-catalyzed enantioselective hydrofunctionalizations of conjugated dienes are challenging reactions that require addressing multiple aspects of selective catalysis. However, the value-added nature of the obtained chiral derivatives and the use of an earth-abundant transition metal have led to increased interest in this field. This Perspective provides an overview of the developments in this area, emphasizing the nature of the hydrofunctionalization agent.
Article
Chemistry, Organic
Shaozi Sun, Qinglong Zhang, Weiwei Zi
Summary: A method for synthesizing allylic chiral hydrazones was presented, and the efficacy of this method was demonstrated by showcasing the transformation reactions of the products into various chiral compounds.
Article
Chemistry, Multidisciplinary
Shang Gao, Jiaming Liu, Diego Troya, Ming Chen
Summary: This article reports a copper-catalyzed reaction that can synthesize ketone compounds with high enantioselectivity and excellent enantioenrichment, providing a valuable platform for further chemical transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Takuya Kurahashi, Seijiro Matsubara
ACCOUNTS OF CHEMICAL RESEARCH
(2015)
Article
Chemistry, Multidisciplinary
Daisuke Sakamaki, Soichiro Yano, Toshiyuki Kobashi, Shu Seki, Takuya Kurahashi, Seijiro Matsubara, Akihiro Ito, Kazuyoshi Tanaka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Tasuku Inami, Takuya Kurahashi, Seijiro Matsubara
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Kazuki Maeda, Takuma Terada, Takahiro Iwamoto, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Multidisciplinary
Kazuki Maeda, Toshifumi Takahashi, Rei Tomifuji, Naoya Hirao, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Organic
Rei Tomifuji, Kazuki Maeda, Toshifumi Takahashi, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Multidisciplinary
Rei Tomifuji, Takuya Kurahashi, Seijiro Matsubara
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Satoru Teranishi, Kazuki Maeda, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Organic
Rei Tomifuji, Shota Masuda, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Organic
Kazuki Maeda, Takuya Kurahashi, Seijiro Matsubara
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Tasuku Inami, Toshifumi Takahashi, Takuya Kurahashi, Seijiro Matsubara
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Physical
Toshifumi Takahashi, Takuya Kurahashi, Seijiro Matsubara
Article
Chemistry, Organic
Rei Tomifuji, Shunpei Murano, Satoru Teranishi, Daiki Kuroda, Takuya Kurahashr, Seijiro Matsubara
Summary: The enantioselective oxa-Diels-Alder reaction of nonactivated substrates using FeCl3 and a 1,1'-bi-2-naphthol (BINOL) derived chiral phosphoric acid as a multiple activation catalyst was successfully achieved in this study. Various oxygen-containing six-membered heterocycles were synthesized in high yields and in an enantioselective manner. Density functional theory (DFT) calculations revealed the synergistic activation of two lone pairs of an aldehyde by both Lewis acidic and Bronsted acidic moieties in the catalyst system to facilitate enantioselective addition reaction of dienes.
Article
Chemistry, Organic
Tasuku Inami, Takuya Kurahashr, Seijiro Matsubara
Summary: A new nickel-catalyzed insertion reaction has been developed, where an alkyne is inserted into a 2-(trifluoromethyl)-1,3-benzothiazole to yield a novel compound. The structure of the intermediate was confirmed through X-ray single-crystal structure analysis and in situ X-ray absorption fine-structure spectroscopy.
Article
Chemistry, Multidisciplinary
Toshifumi Takahashi, Daiki Kuroda, Toru Kuwano, Yuji Yoshida, Takuya Kurahashi, Seijiro Matsubara
CHEMICAL COMMUNICATIONS
(2018)