Article
Chemistry, Multidisciplinary
Mikus Purins, Lucas Eichenberger, Jerome Waser
Summary: We present a mild approach for the synthesis of propargyl silanes from terminal alkynes. A bromonaphthyl-substituted silane was used as a silylmethyl electrophile surrogate, which underwent an aryl-to-alkyl Pd-migration followed by a Sonogashira reaction. A total of 27 propargyl silanes were obtained with yields up to 88%. The resulting products serve as versatile building blocks for addition reactions with electrophiles, triple bond hydrogenation, or silyl group cleavage with acid or fluoride sources.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Seoyeon Kim, Yunjeong Lee, Eun Jin Cho
Summary: In this study, a visible-light-induced selective homocoupling reaction of propargyl bromides to form 1,5-diynes was developed. The key step in the reaction involves the generation of propargyl radicals through a reductive quenching cycle of the photoexcited [Ir(III)]* photocatalyst. The formed 1,5-diyne can be further converted to functionalized indole derivatives through coupling reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
En-He Huang, Ying-Qi Zhang, Da-Qiu Cui, Xin-Qi Zhu, Xiao Li, Long-Wu Ye
Summary: A new copper-catalyzed Si-H bond insertion reaction involving N-propargyl ynamides and hydrosilanes has been discovered, providing an efficient method for the practical and atom-economic synthesis of valuable organosilanes in generally moderate to excellent yields under mild reaction conditions. This reaction also introduces a new pathway for Si-H bond insertion involving vinyl cations as key intermediates.
Article
Chemistry, Organic
Santanu Mondal, Ravindra D. Aher, Venkati Bethi, Yu-Ju Lin, Tohru Taniguchi, Kenji Monde, Fujie Tanaka
Summary: This study reports amine-based catalyst systems for the enantioselective Mannich reactions of pyruvates as nucleophiles. The reactions of pyruvates and cyclic sulfonylimines yielded the desired Mannich products, including those with tetrasubstituted carbon centers, in high yields and enantioselectivities. The choice of acid in the amine-based catalyst system played a key role in the formation of Mannich products with high enantioselectivities.
Article
Chemistry, Organic
Zi-Qi Geng, Chunhui Zhao, Hao-Dong Qian, Si-Jia Li, Hao Peng, Hao Xu
Summary: A Cu/Ag relay catalyzed cascade reaction was used to synthesize chiral triazole-fused pyrazine scaffolds. This method utilized a novel N,N,P-ligand and showed high efficiency, functional group tolerance, excellent enantioselectivities, and a broad substrate scope using readily available starting materials.
Article
Chemistry, Organic
Alexander Baer, Sofia Baer, Moritz Roeder, Rainer Schobert
Summary: The total synthesis of bathymodiolamides A and B was achieved in eight linear steps, starting from Garner's aldehyde and three carboxylic acids, with a yield of 38% and 39%. However, distinct differences were found between the NMR data and antiproliferative activities of the synthetic products and those reported for the natural isolates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Chang-Qing Liu, Hang Li, Bo Wang, Zi-Yi Guo, Yu Wang, Ji-Tan Zhang, Mei-Hua Xie
Summary: A switchable di- and monosulfonylation reaction of propargyl alcohols with sodium sulfinates has been developed, leading to the successful synthesis of (E)-allyl, vinyldisulfones, and propargyl sulfones with good to excellent yields. This protocol has the advantages of using readily available starting materials, a broad substrate scope, and can be conducted in an air-atmosphere and under metal-free conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Hang Yan, Cui Zhang, Jiao-Jiao Han, Si-Si Du, Yuan-Zhao Hua, Min-Can Wang, Guang-Jian Mei, Shi-Kun Jia
Summary: We have developed a new strategy for the enantioselective cascade Michael/acyl transfer reaction of enynones and alpha-hydroxy aryl ketones catalyzed by dinuclear zinc cooperative catalysis. The reaction resulted in the synthesis of structurally diverse chiral 1,5-dicarbonyl compounds with good yields and excellent stereoselectivities. This strategy is notable for its broad substrate scope, high atom economy, and the utilization of enynones as efficient electrophilic acyl transfer reagents in asymmetric cascade reactions for the first time.
Article
Chemistry, Multidisciplinary
Changqing Ye, Yihang Jiao, Mong-Feng Chiou, Yajun Li, Hongli Bao
Summary: This study presents a metal-free method for the synthesis of pentasubstituted pyrroles and hexasubstituted pyrrolines with different substituents and a free amino group. The approach complements previous methods and supports the expansion of the toolbox for synthesizing valuable, but previously inaccessible, highly substituted pyrroles and pyrrolines. Mechanistic studies have been conducted to elucidate the reaction pathway.
Article
Biochemistry & Molecular Biology
Michel Grosse, Kerstin Guenther, Paul M. Jordan, David Roman, Oliver Werz, Christine Beemelmanns
Summary: This study describes the synthesis of delta-hydroxy-beta-keto esters and their evaluation for anti-inflammatory properties. The products exhibited excellent enantioselectivities and surprising structure-activity relationship.
Article
Chemistry, Organic
Golla Ramesh, Bokka Venkat Ramulu, Rengarajan Balamurugan
Summary: The reactivity of o-propargyl alcohol benzaldehydes towards intramolecular electrophile intercepted Meyer-Schuster rearrangement has been significantly increased under Bronsted acid-catalyzed conditions using trimethyl orthoformate as an acetalization reagent. The in situ formed acetal facilitates the intramolecular transfer of the methoxy group, generating the M-S intermediate even in less reactive substrates. The resulting oxocarbenium ion enhances the electrophilicity of the carbonyl, enabling an effective intramolecular trapping of the M-S intermediate to yield indanone derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Hao Fu, Dan Yang, Di Qiu, Chun Hua Yan, Ren Cai, Yaping Du, Weihong Tan
Summary: A facile colloidal chemistry method is reported to obtain three-dimensional supercuboids from two-dimensional ZnSe nanosheets. The highly stable supercuboids can be readily transformed back to nanosheets through an exfoliation process. The potential application of ZnSe nanosheets in catalysis is demonstrated in the aldol condensation reaction.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Yu-Heng Wang, Xi-Rui Wang, Ke-Lan Xu, Zi-Yue Chen, Bo-Wen Pan, Li-Jun Peng, Ying Zhou, Xiong-Li Liu
Summary: This paper describes the first example of umpolung & alpha;-regioselective 1,3-dipolar cycloaddition of optically pure perhydroindole-2-carboxylic acid 1a with pyridinecarboxaldehydes 2. Using this practical method, a wide range of conformationally rigid chiral perhydroindole-bipyridine compounds 3 can be easily prepared with good results, and their diastereoisomers can also be isolated by column chromatography. Furthermore, the diverse derivatization of products 3 into 1,2-oxazinane-containing diverse bipyridine compounds 6 has been successfully demonstrated using m-CPBA as the oxidant.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Angela Y. Thomas, Tommy L. Walls, Brionna N. Nelson, Stafford W. Primeaux, Prem B. Chanda
Summary: In contrast to methyl phenylacetates, methyl arylacetates require a less bulky boron reagent, a bulky amine, and ambient temperature to provide syn-aldols in the enolboration-aldolization reaction. On the other hand, anti-aldol products can be obtained from methyl arylacetates with the presence of Chx(2)BOTf/Et3N at a lower temperature. This study presents the first example of complementary syn- and anti-selective enolboration-aldolization of arylacetates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yu-Heng Wang, Xi-Rui Wang, Ke-Lan Xu, Zi-Yue Chen, Bo-Wen Pan, Li-Jun Peng, Ying Zhou, Xiong-Li Liu
Summary: Here, we describe the first example of umpolung alpha-regioselective 1,3-dipolar cycloaddition between optically pure perhydroindole-2-carboxylic acid 1a and pyridinecarboxaldehydes 2. Using this practical method, a variety of conformationally rigid chiral perhydroindole-bipyridine compounds 3 can be efficiently prepared, and their diastereoisomers can be separated by column chromatography. Additionally, we demonstrate the diverse derivatization of products 3 into 1,2-oxazinane-containing bipyridine compounds 6, facilitated by the oxidant m-CPBA. The high efficiency of these chemical transformations is attributed to the in situ-generated byproduct 3-chlorobenzoic acid, which acts as an internal reuse reagent for subsequent ring-opening and ring-expansion reactions mediated by formal oxygen atom insertion into the carbon-nitrogen bond.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Shengzong Liang, Gerald B. Hammond, Bo Xu
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Deepika Malhotra, Mark S. Mashuta, Gerald B. Hammond, Bo Xu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Manish Kumar, Jacek Jasinski, Gerald B. Hammond, Bo Xu
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Organic
Junbin Han, Zhichao Lu, Gerald B. Hammond, Bo Xu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2014)
Article
Biochemistry & Molecular Biology
Francesca R. Salipur, E. Merit Reyes-Reyes, Bo Xu, Gerald B. Hammond, Paula J. Bates
FREE RADICAL BIOLOGY AND MEDICINE
(2014)
Article
Chemistry, Inorganic & Nuclear
Deepika Malhotra, Leping Liu, Weibo Wang, Mallory Durham, Gerald B. Hammond, Bo Xu
JOURNAL OF FLUORINE CHEMISTRY
(2014)
Article
Chemistry, Multidisciplinary
Otome E. Okoromoba, Junbin Han, Gerald B. Hammond, Bo Xu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Organic
Manish Kumar, Martin Scobie, Mark S. Mashuta, Gerald B. Hammond, Bo Xu
Article
Chemistry, Organic
Manish Kumar, Gerald B. Hammond, Bo Xu
Article
Chemistry, Organic
Bo Xu, Gerald B. Hammond
Article
Chemistry, Organic
Junbin Han, Naoto Shimizu, Zhichao Lu, Hideki Amii, Gerald B. Hammond, Bo Xu
Article
Chemistry, Organic
Weibo Wang, Manish Kumar, Gerald B. Hammond, Bo Xu
Article
Chemistry, Organic
Shengzong Liang, Jacek Jasinski, Gerald B. Hammond, Bo Xu
Article
Chemistry, Organic
Junbin Han, Robert S. Paton, Bo Xu, Gerald B. Hammond
SYNTHESIS-STUTTGART
(2013)
Article
Chemistry, Organic
Kehao Gong, Long Lin, Xinyan Gao, Xiaojun Zeng, Bo Xu, Junbin Han
Summary: We have developed a green and efficient electrochemical method for synthesizing aryl halides, which has broad substrate scope and high functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2023)
