Article
Chemistry, Organic
Hong Li, Rongqiang Tian, Zheng Duan
Summary: A facile and highly atom-economic approach to 2-phosphafurans was reported in this study, with the key step utilizing the Lewis acidity of electrophilic phosphinidenes to induce an intramolecular cyclization with enones. Dearomative hetero-Diels-Alder reactions of 2-phosphafurans provided two series of bicyclic phosphacycles, representing a rare synthetic application of the Lewis acidity of electrophilic phosphinidene complexes in phosphinidene chemistry.
Article
Chemistry, Organic
Weiwei Jin, Shouyun Yu
Summary: The photoinduced and palladium-catalyzed remote desaturation of O-acyl hydroxamides to unsaturated amides under mild conditions has been achieved efficiently and selectively. This method features good site-selectivity, is terminal oxidant-free, and produces moderate to excellent yields for a variety of unsaturated amides, enabling late-stage desaturation of complex and biologically important molecules.
Article
Chemistry, Multidisciplinary
Ryan Phelps, Andrew J. Orr-Ewing
Summary: This study utilizes ultrafast time-resolved infrared absorption spectroscopy to investigate the photoexcitation and reaction processes of a-diazocarbonyl compounds, providing direct observation of the competition between ylide formation and C-H insertion. The specific solvation dynamics of THF-derived ylide and its interactions with hydrogen-bond donors and lithium cations are studied, and the coordination preferences and hybridization changes of the ylidic carbon atom are characterized.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Evgeny M. Buev, Polina A. Khardina, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
Summary: In this study, a multicomponent synthesis of pyrrolidines was performed using a Wittig/Huisgen tandem reaction, which allows the simultaneous generation of alkene and azomethine ylide from the same carbonyl compound. This approach successfully constructed highly substituted dispiropyrrolidines as well as simple 3-substituted pyrrolidines.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Ning Xian, Jiang Yin, Xiaochen Ji, Guo-Jun Deng, Huawen Huang
Summary: The visible-light-induced photoredox carbon radical formation from aqueous sulfoxonium ylides has been demonstrated for the first time. Direct reduction of sulfoxonium ylides by H2O generates hydrocarbon compounds efficiently, while the use of additional alkenes as radical acceptors changes the chemical reactivity to achieve alkene carboarylation of N-arylacrylamides. Mechanistic studies reveal two different reaction pathways involved in the carbon radical formation from aqueous sulfoxonium ylides resulting in reduction to release dimethyl sulfone and carboarylation to form DMSO.
Article
Biochemistry & Molecular Biology
Ignacy Janicki, Piotr Kielbasinski
Summary: This report presents new, easily accessible reagents for highly Z-selective HWE reactions, demonstrating very good Z-selectivity and high yields in most cases. The application of these new reagents may provide a valuable and practical alternative to the well-established Still-Gennari or Ando Z-selective carbonyl group olefination protocols.
Article
Chemistry, Applied
Sandip Sambhaji Vagh, Bo-Jhih Hou, Athukuri Edukondalu, Pin-Ching Wang, Yi-Ru Chen, Wenwei Lin
Summary: A phosphine-mediated reaction was reported for the construction of spirocyclopenta[c]chromene-indolinones via a Rauhut-Currier (RC)-type/acyl transfer/Wittig sequence. Extensive investigations revealed key steps including chemoselective phosphine addition, O-acylation reaction, and the subsequent Wittig reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Murali Boosa, Divya Rohini Yennamaneni, Durgaiah Chevella, Vasu Amrutham, Krishna Sai Gajula, Ramulamma Madasu, Venugopal Akula, Narender Nama
Summary: This study investigates the direct addition reaction between beta-diketone and various alcohols and alkenes using solid acid zeolites (HY and H beta) as catalysts. The presence of acidic sites and porous structures significantly affect the catalytic activity. The results demonstrate that these zeolite catalysts exhibit high efficiency for nucleophilic addition/substitution reactions, and can be easily separated from the reaction mixture through simple filtration process.
Article
Chemistry, Organic
Masanori Shigeno, Akihisa Kajima, Kunihito Nakaji, Kanako Nozawa-Kumada, Yoshinori Kondo
Summary: The amide base generated in situ from tetramethylammonium fluoride and N(TMS)(3) catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound, and is applicable to a variety of allylbenzenes with functional groups as coupling partners. Role of trans beta-methyl stilbenes in product formation is also elucidated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Ignacy Janicki, Piotr Kielbasinski
Summary: The Z-selective Still-Gennari and Ando modifications of the Horner-Wadsworth-Emmons reaction are valuable synthetic tools in organic chemistry. A purification-free procedure for the synthesis of these reagents has been presented, resulting in high purity products on a gram scale. Additionally, a novel Still-Gennari type reagent has been synthesized, which may exhibit improved Z-selectivity in olefinations.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Qian Wang, Jiang Liu, Nana Wang, Romana Pajkert, Haibo Mei, Gerd-Volker Roschenthaler, Jianlin Han
Summary: We report a one-pot reaction for the synthesis of azo-containing alpha-fluorovinylphosphonates using aza-Wittig reagents. Mechanism studies reveal a pathway involving aza-Wittig reaction, water addition, and C-F bond cleavage. This reaction provides a strategy for the synthesis of alpha-fluorovinylphosphonate derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Liyan Fu, Qiang Chen, Yasushi Nishihara
Summary: This paper reviews recent developments in cross-coupling reactions forming C-C bonds by cleaving C(sp(2))-F bonds, including conventional activation and decarbonylative or carbonyl-retentive methods. New protocols for forming various C-C bonds via transition-metal-catalyzed cleavage of C(sp(2))-F bonds are described.
Article
Chemistry, Multidisciplinary
Yannan Liu, Shuai Fu, Dominik L. Pastoetter, Arafat Hossain Khan, Yingying Zhang, Arezoo Dianat, Shunqi Xu, Zhongquan Liao, Marcus Richter, Minghao Yu, Miroslav Polozij, Eike Brunner, Gianaurelio Cuniberti, Thomas Heine, Mischa Bonn, Hai Wang, Xinliang Feng
Summary: The ability to efficiently synthesize vinylene-linked two-dimensional covalent organic frameworks (V-2D-COFs) is crucial for their potential applications in electronics and optoelectronics. In this study, the E/Z selectivity of the Wittig reaction was tailored by using a suitable catalyst and increasing the reaction temperature, resulting in the successful synthesis of four crystalline V-2D-COFs. The high charge carrier mobilities and good crystallinity of these V-2D-COFs were demonstrated through non-contact terahertz spectroscopy analysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Isabelle Nathalie-Marie Leibler, Makeda A. Tekle-Smith, Abigail G. Doyle
Summary: The study introduces a novel method using nucleophilic coupling partners through successive hydrogen atom transfer and oxidative radical-polar crossover. This strategy transforms C(sp(3))-H bonds into carbocations, enabling diverse bond formations with various nucleophiles and providing new site-selectivity for late-stage C(sp(3))-H functionalization.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Moena Kato, Koushik Ghosh, Yuji Nishii, Masahiro Miura
Summary: The study reports a rhodium-catalysed direct formylmethylation using vinylene carbonate as an ethynol equivalent. The developed catalytic system is further applied in the oxidant-free production of esters with hydrogen gas liberation. Control experiments are conducted to elucidate the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2021)
