Article
Chemistry, Organic
Di Wu, Chengcheng Li, Yongjie Duan, Hongquan Yin, Fu-Xue Chen
Summary: In this study, a chlorothiocyanato difunctionalization reaction was achieved, and various alpha-chlorothio/selenocyanato difunctional ketones were synthesized through a one-pot strategy from beta-keto acids. The high yield and wide scope of substrates make this approach more practical for the synthesis of alpha-substituented difunctional ketones.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Nand Gopal Giri, Ismail Althagafi, Trisha Ghatak, Ramendra Pratap
Summary: We have discovered a base-mediated method for the conversion of 3,3-bis(methylthio)-1-arylprop-2-en-1-ones to versatile active methylene compounds (beta-keto esters). By modifying the method, we achieved the synthesis of the target compounds directly from aryl methyl ketone with excellent yields. Cyclopropyl methyl ketone was also tested as a source of aliphatic ketone, yielding the desired product under similar reaction conditions.
Article
Chemistry, Organic
Ping Li, Fan Yang, Guiwen Hu, Xiaoxiang Zhang
Summary: A novel and efficient synthetic method was developed for the preparation of various pyrroloindolines from 2-alkynyl arylazides and thioacetamides. The reaction was carried out in a one-pot process under mild reaction conditions to afford the products in moderate to good yields, showing potential for use in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Longlong Song, Dan Ni, Wangyujing Han, Jie Tang, Fan Yang, Shunying Liu
Summary: A green and highly efficient one-pot method for the synthesis of alpha-diaryl-beta-alkynol derivatives in water at room temperature was developed using the cocatalysis of a Lewis acid and meso-tetraphenylporphyrin iron(III) chloride (FeTPPCl). Water also acts as the third reactant for the one-pot transformation, which showed good to excellent yields and a broad substrate scope. The FeTPPCl catalyst can be directly reused four times with a slight discount in yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Venkati Bethi, Fujie Tanaka
Summary: Catalytic asymmetric Mannich reactions of beta-ketocarbonyl derivatives, such as beta-ketoesters and (2-oxopropyl)-phosphonate, have been reported. These reactions result in the formation of C-C bonds at the gamma-position of the beta-ketocarbonyl derivatives with high enantioselectivities. The reversible bond formation at the alpha-position of the beta-ketoester and the stable formation of the gamma-position-reacted product delta-amino beta-ketoester derivative are attributed to the dynamic kinetic process under catalytic conditions.
Article
Chemistry, Multidisciplinary
Pragya Sharma, Neha Taneja, Sanjay Singh, Chinmoy K. Hazra
Summary: A three-component, solvent-dependent, Bronsted-acid-catalyzed reaction has been developed for the synthesis of potential drug candidate 3-aryl-1-indanones. This reaction features high regioselectivity, broad substrate generality, easy scalability, and diverse starting materials. Detailed mechanistic insight leads to a feasible reaction pathway.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Oleg L. Tok, Jonathan Bould, Michal Dusek, Josef Cvacka
Summary: The reaction of vinyl(alkynyl)silanes with 9-BBN-H leads to the formation of 5-R-4-(9-BBN)-2,3-dihydro-1H-siloles, while treatment of bis(alkynyl)silanes with 9-BBN-H followed by methanolysis yields 5-R-4-(9-BBN)-2,5-dihydro-1H-siloles. The reaction proceeds via a double 1,2-hydroboration of the terminal triple bond followed by ring closure, resulting in different dihydrosiloles depending on the substituent R. Protonation of allylic BBN group with MeOH results in the exclusive formation of 4-(9-BBN)-2,5-dihydrosiloles. Additionally, tri- and tetraalkynes containing a terminal triple bond react with 9-BBN-H to form 1,2,6,6a-tetrahydro-1,6-disilapentalenes and 2,6,7,7a-tetrahydro-1,6,7-trisila-1H-cyclopenta[a]pentalenes, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Fan Yang, Shijie Xu, Hui Fan, Xuechun Zhao, Xiaoxiang Zhang
Summary: The novel synthetic method described in this study utilizes various 2-alkynyl arylazides to efficiently produce products in moderate to good yields under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kazuki Tomota, Yuki Izumi, Kazuki Nakanishi, Masaaki Nakamoto, Hiroto Yoshida
Summary: A direct and transition metal-free method for the installation of B(dan) into organic frameworks has been developed. Heteroaryl-H bonds can be transformed into heteroaryl-B(dan) bonds through deprotonation. The resulting heteroaryl-B(dan) compounds, which are typically difficult to access, can undergo direct Suzuki-Miyaura coupling. The method has also been demonstrated to be applicable to silicon nucleophiles, leading to the formation of Lewis acidity-diminished stable silyl-B(dan) and -B(aam) in one pot.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhi-Cheng Yu, You Zhou, Xiang-Long Chen, Jin-Tian Ma, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
Summary: A reductive coupling reaction was established for the synthesis of diaryl 1,2-dicarbonyl compounds from aryl methyl ketones. The reaction involves C(CO)-C(sp3) bond cleavage and proceeds through an electron transfer process. Notably, this reaction is simple to operate, has mild reaction conditions, and is applicable to a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jingyu Gao, Yi Li, Nengzhong Wang, Zhiyue Li, Nianyu Huang, Hui Yao
Summary: A one-pot synthesis of 2,3,4-unprotected β-N-glycopyranosides from glycals and amines with exclusive β-stereoselectivity under room temperature conditions is reported. This method, achieved via palladium-catalyzed Tsuji-Trost amination followed by dihydroxylation directly, can tolerate anilines, heterocyclic aromatic amines, and N,O-dimethylhydroxylamine. Particularly, the reaction of primary amines and glycals has not been reported before. Furthermore, this protocol has been successfully applied in the modification of clinical drugs (prazosin, imiquimod) and the construction of an analogue of natural product amphimedoside A.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Kaori Ando, Chika Takaba, Masahiro Kodama
Summary: In this study, a convenient and high-yield synthesis method for Z-α,β-unsaturated esters was developed. By using a one-pot oxidation/olefination reaction with suitable catalysts and reagents, the desired product with high selectivity could be obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jing Shi, Xue-Wang Gao, Qing-Xiao Tong, Jian-Ji Zhong
Summary: This novel strategy combines light-promotion and tertiary-amine assistance to efficiently access beta-hydroxysulfides. In contrast to traditional methods, this approach offers mild reaction conditions, high efficiency, and excellent functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kai N. Sands, Benjamin S. Gelfand, Thomas G. Back
Summary: Aryl selenonic acids were synthesized from aryl bromides via a one-pot method, with yields ranging from 77-90%. The synthesis involved metalation, selenation, oxidation with hydrogen peroxide, and ion exchange. One derivative readily dehydrated to form a cyclic selenonic ester, while two minor byproducts were identified as mixed salts of aryl selenonic acids with either aryl seleninic or selenious acid through X-ray crystallography.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhe Fan, Shao-Fei Ni, Jin-Yu Pang, Li-Ting Guo, Hao Yang, Ke Li, Cheng Ma, Ji-Kai Liu, Bin Wu, Jin-Ming Yang
Summary: A novel strategy for the formation of copper carbene and a Cu(I)-catalyzed cross-coupling protocol for the synthesis of 7-alkynyl cycloheptatrienes have been reported in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
