Article
Chemistry, Organic
Ke Li, Zhenjie Gan, Er-Qing Li, Zheng Duan
Summary: A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Article
Chemistry, Organic
Casper Larsen Barlose, Jonas Faghtmann, Rene Slot Bitsch, Joseph Daniel Gbubele, Karl Anker Jorgensen
Summary: The combination of asymmetric organocatalysis with the (pseudo)-halogen effect allows for the efficient formation of chiral norcarane scaffolds. These scaffolds can easily undergo rearrangements or lactonization to form intricate chiral ring structures.
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunxia Li, Yunfeng Du, Yiming Liu, Rongfang Liu, Rong Zhou
Summary: Phosphine-catalyzed reactions enable efficient synthesis of polysubstituted olefins or multifunctional dienes. The study reveals the divergent reactivity of alkynoates toward electrophiles under organophosphine catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wei Sun, Meng-Yang Hu, Zhan-Sheng Lu, Ming-Yao Huang, Xin-Yu Zhang, Shou-Fei Zhu
Summary: This article reports a method for stereoselective transformation using an iron catalyst to synthesize Z-allylsilanes with high regioselectivity and exclusive stereoselectivity from E/Z mixtures. The mechanism of this reaction differs from previously reported mechanisms.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Joshua Atta-Kumi, George Baffour Pipim, Ernest Opoku
Summary: The mechanism of tandem reactions between 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole and different types of dienes has been studied. The initial [4+2] cycloaddition is the rate-determining step, and the stereochemistry of the tandem adduct is determined by the [3+2] step. The polarity of these reactions is influenced by two factors: the nature of the heteroatom present on the diene molecule and the size of the cyclic diene.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2023)
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, Applied
Daniel Gavina, Marcos Escolano, Lia Sotorrios, Enrique Gomez-Bengoa, Fernando Lopez-Ortiz, Maria Sanchez-Rosello, Carlos del Pozo
Summary: This study reveals the different reactivity of fluorinated conjugated sulfinyl imines with dicyanoalkenes in organic synthesis. Specifically, tert-butyl sulfinyl imines undergo cycloaromatization reaction with dicyanoalkenes, leading to valuable trifluoromethyl arenes. p-tolyl sulfinyl imines, on the other hand, produce a complex tetracyclic skeleton. 1-indanone-derived dicyanoalkenes interrupt the aromatization process, resulting in a new family of diene derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Peter Wonneberger, Nils Koenig, Menyhart B. Sarosi, Evamarie Hey-Hawkins
Summary: Reduction of 1-phospha-2-azanorbornene derivative leads to formation of a novel compound 1-phosphabicyclo[3.2.1]octa-2,5-diene and an unusual 2H-phosphole dimer. Additionally, 3H-phospholes were found to potentially act as dienophile in the dimerisation reaction under elevated temperatures, contrary to previous assumptions of their synthetic irrelevance.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Physical
Geoffrey Dumonteil, Sabine Berteina-Raboin
Summary: This review focuses on commonly used synthetic methods to obtain molecules with conjugated dienes. The methods discussed mainly involve cross-coupling reactions using metals such as nickel, palladium, ruthenium, cobalt, cobalt/zinc, manganese, zirconium, or iron. Through examples, the review explores the synthesis of natural molecules or their analogues. Specifically, the total synthesis of the phytohormone Acid Abscisic (ABA) by the author's team is discussed, which involves the development of a conjugated diene chain.
Article
Chemistry, Organic
Shunian Li, Haifeng Lu, Zhenghu Xu, Fang Wei
Summary: The efficient Ni(ii)/Feng ligand-catalyzed asymmetric hetero-Diels-Alder reaction between conjugated vinyl azides and carbonyl groups reported in this study provides a platform for the synthesis of complicated chiral azido polycycles in high yields and excellent enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Qi-Ying Liao, Chao Ma, Yu-Chao Wang, Shao-Qian Yang, Jiang-Shan Ma, Zhi-Tao He
Summary: Because of the widespread applications of optically active alkyl fluorides in medicinal and agrochemicals, the study of enantioselective and stereodivergent construction of alkyl fluorides remains highly desirable. In this study, a palladium-catalyzed enantioselective hydromonofluoroalkylation reaction was developed to achieve this goal.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Shunya Morita, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: The three-component reactions of nitroalkanes, acrylamides, and aldehydes using catalytic amount of KOH in DMSO resulted in the formation of beta '-hydroxy-gamma-nitro amides. Mechanistic studies showed that the reactions proceeded through domino Michael/aldol reactions.
Article
Chemistry, Physical
Zhishuai Geng, M. G. Finn
CHEMISTRY OF MATERIALS
(2016)
Article
Chemistry, Physical
Bo Song, Ji Il Choi, Yuntong Zhu, Zhishuai Geng, Le Zhang, Ziyin Lin, Chia-chi Tuan, Kyoung-sik Moon, Ching-ping Wong
CHEMISTRY OF MATERIALS
(2016)
Article
Chemistry, Multidisciplinary
Zhishuai Geng, M. G. Finn
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Physical
Bo Song, Jingxiang Zhao, Mingjun Wang, Jeffrey Mullavey, Yuntong Zhu, Zhishuai Geng, Dongchang Chen, Yong Ding, Kyoung-sk Moon, Meilin Liu, Ching-Ping Wong
Article
Chemistry, Multidisciplinary
Parikshit Gogoi, Zhe Zhang, Zhishuai Geng, Wei Liu, Weize Hu, Yulin Deng
Article
Chemistry, Multidisciplinary
Xu He, Haiyang Zou, Zhishuai Geng, Xingfu Wang, Wenbo Ding, Fei Hu, Yunlong Zi, Cheng Xu, Steven L. Zhang, Hua Yu, Minyi Xu, Wei Zhang, Canhui Lu, Zhong Lin Wang
ADVANCED FUNCTIONAL MATERIALS
(2018)
Review
Chemistry, Multidisciplinary
Peizhong Xie, Wenqing Lai, Zhishuai Geng, You Huang, Ruyu Chen
CHEMISTRY-AN ASIAN JOURNAL
(2012)
Article
Chemistry, Physical
Zhishuai Geng, Mark Garren, M. G. Finn
CHEMISTRY OF MATERIALS
(2018)
Article
Biochemistry & Molecular Biology
Pranav P. Kalelkar, Zhishuai Geng, M. G. Finn, David M. Collard
Editorial Material
Chemistry, Multidisciplinary
Zhishuai Geng, Jongbok Lee, Craig J. Hawker
Article
Nanoscience & Nanotechnology
Boyou Hou, Wenyuan Zhang, Hongyu Lu, Kunpeng Song, Zhishuai Geng, Xinming Ye, Ye-Tang Pan, Wenchao Zhang, Rongjie Yang
Summary: The hybridization of ZIF-67 with octacarboxyl POSS forms novel metal POSS-organic frameworks, improving the flame retardancy and mechanical properties of epoxy resin.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Organic
Jiawen Wu, Cunbo Wei, Fen Zhao, Wenqian Du, Zhishuai Geng, Zhonghua Xia
Summary: A convenient and mild gold-catalyzed protocol for the intermolecular coupling of o-alkynylphenols with haloalkynes to yield vinyl benzofurans has been reported. The reaction involves the intramolecular cyclization of the o-alkynylphenol to benzofuran, followed by a selective hydroarylation of the benzofuran to haloalkyne. Computational studies have provided insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Lindsay L. Robinson, Eden S. Taddese, Jeffrey L. Self, Christopher M. Bates, Javier Read de Alaniz, Zhishuai Geng, Craig J. Hawker
Summary: In this study, a catalyst-free covalent adaptable network (CAN) was developed by using a cross-linker with sulfur-atom neighboring group participation (NGP) to increase the rate of bond exchange. The network exhibited thermally mediated cross-link interchange and associated flow behavior, enabling reprocessing over multiple damage and repair cycles. Additionally, the NGP-based CANs were chemically recyclable.
Article
Engineering, Environmental
Xiaoning Song, Boyou Hou, Zhengde Han, Ye-Tang Pan, Zhishuai Geng, Laia Haurie Ibarra, Rongjie Yang
Summary: We successfully designed a polyphosphazene hollow hybrid material via the polymerization of phosphazene accompanied by the etching of ZIF-67 and cobalt compounds by generated HCl. The hybrid material (CPPHS) was composed of cobalt-doped polyphosphazene hollow sub-micron polyhedrons (CP) and polyphosphazene hollow nanospheres (PHNS) with different dimensions and magnitudes of sizes. Adding 2.0 wt% CPPHS to epoxy resin increased the limiting oxygen index by 27.6%, while reducing the peak heat release rate and total smoke production by 40.1% and 38.8%, respectively.
CHEMICAL ENGINEERING JOURNAL
(2023)
