Article
Chemistry, Applied
Antonio Arcadi, Giancarlo Fabrizi, Antonella Goggiamani, Antonia Iazzetti, Federica Iavarone, Federico Marrone, Giulia Mazzoccanti, Alessio Sferrazza
Summary: A palladium-catalyzed domino approach has been developed for the synthesis of challenging phenanthrene derivatives. The procedure involves a sequence of oxidative homocoupling, cyclization, and oxidation starting from deoxybenzoin derivatives ortho-halogenated. Good assembly efficiency and functional group tolerance were observed with yields ranging from moderate to excellent. A plausible reaction mechanism has been proposed based on experimental results and literature data.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Bin Shi, Jia-Bin Liu, Ze-Tian Wang, Liang Wang, Yu Lan, Liang-Qiu Lu, Wen-Jing Xiao
Summary: This study presents a new method for the synthesis of chiral endocyclic allenes with high efficiency and enantioselectivity, using a relay strategy that combines Pd-catalyzed [3+2] annulation and enyne-Cope rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Qi Li, Zi-Lu Wang, Huan-Xuan Lu, Yun-He Xu
Summary: A copper-catalyzed 1,4-protosilylation of alpha-alkynyl-enones has been developed to prepare functionalized chiral homoallenylsilanes with a contiguous stereogenic center and axis, showing good yields and excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Multidisciplinary
Nurbey Gulia, Jaroslaw Fornalski, Adrianna Gumienna, Malgorzata Ambroziak, Slawomir Szafert
Summary: This study reports a method of palladium-catalyzed C-H arylation assisted with a 3,4,4-trimethylpyrazol-5-on directing group, which selectively provides mono- and di-ortho-arylated products. The steric hindrance between the directing group and the already introduced aryl substituent enables control of mono- vs. diarylation selectivity by the reaction temperature. A series of monosubstituted and disubstituted derivatives were obtained in good yields. In addition, a one-pot procedure for unsymmetrical double-arylation to give corresponding products was developed, and the synthesis and X-ray study of intermediate palladium metallacycles were conducted. The decarboxylative cleavage of the pyrazolone directing group under mild conditions gave synthetically useful hydrazones. Overall, this solution provides an alternative synthetic pathway for ortho arylated derivatives of arylhydrazines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Jie Lin, Minqiang Jia, Shengming Ma
Summary: The paper presents the successful development of the palladium-catalyzed exclusive 2,3-allenylation reaction of oxindoles with 2,3-allenylic carbonates, along with a proposed rationale for the selectivity of this reaction over the expected 1,3-alkadienylation.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Aranya Das, Sudipto Debnath, Poulami Hota, Tuluma Das, Dilip K. Maiti
Summary: Unprecedented metal-free cyclization catalysis reactions are developed to synthesize 3-amino-4-benzoyl biphenyls and arylacridones with high atom economy. Catalytic K2CO3 is used to achieve rapid dual C-C-coupled cyclization between beta-keto enamines and cinnamaldehydes, while molecular I-2 acts as a catalyst for C(sp(2))-H functionalized C-N bond-forming cyclization to yield valuable arylacridones. Plausible mechanisms for the new cyclization reactions are predicted through control experiments and ESI-MS analyses.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yang Yuan, Fu-Peng Wu, Anke Spannenberg, Xiao-Feng Wu
Summary: An efficient strategy for synthesizing beta-geminal-diboryl ketones through a Cu/Pd-catalyzed borocarbonylative trifunctionalization of readily available alkynes and allenes has been reported. This method shows broad functional group tolerance and has the potential to advance the field of organic synthesis. Mechanistic studies suggest that the reaction proceeds through a borocarbonylation/hydroboration cascade of both alkynes and allenes.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Organic
Maxym Tansky, Zipeng Gu, Robert J. Comito
Summary: This report introduces a new method for the synthesis of bis(pyrazolyl)alkanes, avoiding common issues in traditional methods and suitable for systematic ligand optimization. Additionally, new reactants including pyrazoles and aldehydes have been explored, providing a new direction for the development of novel catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jun Dai, Long Li, Ronghua Ye, Shan Wang, Yingcheng Wang, Fangzhi Peng, Zhihui Shao
Summary: A method for the asymmetric construction of functionalized acyclic all-carbon quaternary stereocenters and 1,3-nonadjacent stereoelements has been developed through the use of an unknown acyclic secondary-secondary diamine as the organocatalyst, in combination with a metal catalyst. This study challenges the belief that secondary-secondary diamines are unsuitable for use as organocatalysts in organo/metal dual catalysis. The method enables the synthesis of axially chiral allene-containing acyclic all-carbon quaternary stereocenters and 1,3-nonadjacent stereoelements bearing both allenyl axial chirality and central chirality in good yields with high enantio- and diastereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Li-Ping Pang, Xin-Yu Li, Shi-Cheng Ren, Hong-Min Lin, Ying-Chun Wang, Ying-Ming Pan, Hai-Tao Tang
Summary: In this study, a single-atom Pd-metalated polymer was used as a catalyst to achieve regioselective hydrosilylation of allenes. The catalyst showed high efficiency and selectivity, and could be recycled multiple times in a continuous flow system.
Article
Chemistry, Inorganic & Nuclear
Yan Xu, Hong Yi, Martin Oestreich
Summary: This study reports a direct synthesis of enantioenriched allenylsilanes from racemic a-silylated propargylic bromides through an enantioconvergent nickel-catalyzed cross-coupling. The regioselectivity is controlled by the bulky silyl group, and the bond formation occurs exclusively at the y-position of the propargyl electrophile. The level of enantioselection induced by a chiral Pybox ligand is moderate.
Article
Chemistry, Multidisciplinary
Yinsong Zhao, Shaozhong Ge
Summary: A chromium-catalyzed reaction has been developed for the synthesis of boryl-functionalized skipped dienes. By utilizing a dimerization/hydroboration process, the target product can be obtained efficiently and with good selectivity. EPR spectroscopic studies suggest that the reaction proceeds through a chromium(I) hydride intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Kai Ji, Ka Lu, Jie Huang, Zi-Hao Li, Hua Ke, Zhi-Min Chen
Summary: A Bronsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time, along with a solvent-controlled divergent synthesis of sulfides. The study showed that the choice of solvent influenced the type of products obtained, with acetonitrile yielding allylic sulfides and dichloromethane yielding thiochromane derivatives. The regioselectivity of hydrothiolation was investigated using density functional theory calculations.
Article
Chemistry, Organic
Baolei Wang, Marius-Georgian Constantin, Simarpreet Singh, Yuqiao Zhou, Rebecca L. Davis, F. G. West
Summary: Keto-substituted 1,2-cyclohexadienes were generated through base-mediated elimination and dimerized via an unprecedented formal hetero-Diels-Alder process, followed by hydration. These highly reactive cyclic allene intermediates showed high regio- and diastereoselectivity in Diels-Alder reactions, and could also react with enamine dienophiles in a hetero-Diels-Alder process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Sami Chniti, Laszlo Kollar, Attila Benyei, Attila Takacs
Summary: This research investigates the aminocarbonylation reaction of 6-iodoquinoline, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. The study shows that reaction conditions significantly influence the formation of amides and ketoamides, and by optimizing the conditions, selective synthesis of the desired products can be achieved.
