Article
Chemistry, Organic
Chaolei Liu, Zheng Liang, Ayisenbati Jialingbieke, Jian Gao, Ding Du
Summary: A novel method for the facile assembly of alpha-sulfonyl ketones through N-heterocyclic carbene (NHC)-catalyzed radical-mediated sulfonyl methylation of aldehydes has been developed. The reaction involves single-electron transfer reduction of alpha-iodosulfones by NHC-bound Breslow intermediates, followed by radical-radical coupling to form the target compounds. Furthermore, the catalytic system is also effective for the difunctionalization of styrenes and 1,3-enynes via a three-component radical relay process.
Article
Chemistry, Organic
Xiaoshuo Wang, Shubing Shu, Xiaojing Wang, Renshi Luo, Xiayi Ming, Tao Wang, Zhenming Zhang
Summary: A facile electrochemical method has been developed for the sulfonylative cycloether-ification of unsaturated alcohols and acids, utilizing sulfonyl hydrazides. The reaction proceeds via electro-oxidation, radical addition, and intramolecular oxygen nucleophilic process. This methodology demonstrates broad substrate scope and good functional group compatibility, providing a valuable synthetic tool for the formation of oxygen heterocycles. Control experiments indicate that the N-H bonds of sulfonyl hydrazide are non-essential.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sumit Das, Shantonu Roy, Arup Bhowmik, Writhabrata Sarkar, Imtiaj Mondal, Aniket Mishra, Shubhra Jyoti Saha, Sudip Karmakar, Indubhusan Deb
Summary: This study establishes a straightforward strategy for the direct incorporation of sulfonyl units into a xanthene moiety, yielding xanthen-9-sulfone derivatives in good to excellent yields via metal-free radical-radical cross-coupling reaction. The methodology uses easily accessible starting materials and proceeds efficiently under simple reaction conditions with a high degree of functional group compatibility.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Rongxiang Chen, Shaohong Xu, Fumin Shen, Canran Xu, Kaikai Wang, Zhanyong Wang, Lantao Liu
Summary: This method allows for efficient synthesis of sulfonyl chlorides/bromides and their conversion to other functional groups, enabling the synthesis of complex compounds. The reactions are highly selective, simple, and clean, with excellent yields.
Article
Chemistry, Organic
Peng-Ju Xia, Fu Liu, Shu-Hui Li, Jun-An Xiao
Summary: This strategy utilizes tunable photoredox catalysis and manipulation of catalyst and solvent to achieve chlorosulfonylation and oxysulfonylation of alpha-trifluoromethylstyrenes, resulting in diverse bifunctional products with up to 95% yield and excellent functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Deepak Bhadoria, Rajesh Kumar, Ruchir Kant, Atul Kumar
Summary: A simplified method for the synthesis of various functionalized olefins has been developed, which is efficient, does not require pre-treatment, and does not involve the use of catalysts or oxidants.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ming-Ming Li, Lei Cheng, Li-Jun Xiao, Jian-Hua Xie, Qi-Lin Zhou
Summary: The highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides was achieved using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand, providing a practical method for synthesizing chiral allylic sulfones. Mechanistic studies indicated that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product, with the enantioselectivity determined in the conversion from the intermediate to the product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Navin Yadav, Soumen Payra, Jarugu Narasimha Moorthy
Summary: A metal-free and green iodine-catalyzed protocol is described for the synthesis of unsymmetrical thiosulfonates. The reactions occur at room temperature and provide good-to-excellent yields of the desired products.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dong Yi, Linying He, Zhongyu Qi, Zhijie Zhang, Mengshun Li, Ji Lu, Jun Wei, Xi Du, Qiang Fu, Siping Wei
Summary: Alkoxy radical-mediated carbon-carbon bond cleavage is an effective synthetic strategy that allows for selective cleavage of carbon-carbon bonds, providing a convenient route for the synthesis of valuable compounds and enabling the construction of complex molecular architectures.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Seok-Hyeon Cheong, Daeun Kim, Huyen Tran Dang, Dongwook Kim, Bora Seo, Minserk Cheong, Soon Hyeok Hong, Hyunjoo Lee
Summary: This study reports that the anionic form of palladium, PdCl(4)(2-), can effectively convert methane to methyl trifluoroacetate (MeTFA) in the K2S2O8-HTFA oxidation system. The anionic catalyst form increases Pd solubility in the HTFA solvent, facilitating the conversion to the real catalytic species. The role of trifluoroacetic anhydride (TFAA) in removing water produced by the oxidant and oxidation byproduct is also identified for the first time.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Binoyargha Dam, Ashish Kumar Sahoo, Bhisma K. Patel
Summary: This study presents a method for the blue-light induced synthesis of beta-keto sulfones using commercially available compounds and a recyclable photocatalyst. Mechanistic investigation revealed different pathways for the formation of beta-keto sulfones from different reactants. The method also enabled the synthesis of biologically active compounds and post-synthetic modifications. Additionally, the method demonstrated good environmental friendliness and wide applicability with the absence of metal, base, and ligands.
Review
Chemistry, Multidisciplinary
Bao-Chen Qian, Chao-Zhe Zhu, Guang-Bin Shen
Summary: Sulfonyl hydrazides are considered as alternatives to widely used sulfinic acids and their salts or sulfonyl halides in organic synthesis or as active pharmaceutical substances. They are versatile building blocks for constructing C-S bonds, C-C bonds, and even C-N bonds. The recent developments in electrosynthesis using sulfonyl hydrazides as radical precursors have revealed unique and novel synthesis reactions, including cascade reactions and continuous flow methods.
Article
Chemistry, Multidisciplinary
Yunpeng Cao, Xinmou Wang, Haoran Jiao, Hongjian Song, Yuxiu Liu, Qingmin Wang
Summary: A highly efficient and environmentally friendly protocol for Smiles rearrangements is developed in this study, which eliminates the release of SO2 and allows for mild functionalization of compounds.
Article
Chemistry, Organic
Jin Kyu Park, Jonghoon Oh, Sunwoo Lee
Summary: The synthesis of sulfonyl fluorides via the reaction of sulfonyl hydrazides and Et3N•3HF under electrochemical conditions is reported. Various sulfonyl fluorides were obtained in good yields. n-Bu4NI was found to act as an electrolyte and a redox catalyst.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Guoping Yang, Xuanjie Xie, Mengyuan Cheng, Xiaofei Gao, Xiaoling Lin, Ke Li, Yuanyuan Cheng, Yufeng Liu
Summary: A simple and efficient method for the synthesis of pyrazoles has been developed using silicotungstic acid catalyzed cyclization. The reaction involves the reaction of epoxides/aldehydes with sulfonyl hydrazides, producing 3,4-disubstituted 1H-pyrazoles. The use of this method provides a green approach for the construction of these compounds, using an abundant and non-toxic catalyst.
CHINESE CHEMICAL LETTERS
(2022)
