Article
Chemistry, Organic
Zichen Pan, Xiuqi Wang, Shuaishuai Zhao, Hongping Deng, Mengtao Ma, Fei Xue
Summary: We have successfully developed a convergent paired electrolysis strategy for defluorinative thiolation using thiols and gem-difluoroalkenes as precursors. This protocol shows excellent tolerance towards a wide range of functional groups, demonstrated by successful late-stage defluorothiolation of complex molecules. Additionally, this strategy enables gram-scale synthesis by efficiently utilizing both anodic oxidation and cathodic reduction processes.
Article
Chemistry, Organic
Jun-Qi Zhang, Jiayue Liu, Dandan Hu, Jinyu Song, Guorong Zhu, Hongjun Ren
Summary: A scalable cyanation method for the synthesis of (hetero)arylacetonitrile derivatives from gem-difluoroalkenes has been developed. This method offers mild reaction conditions, excellent yields, a wide range of applicable substrates, and tolerance to various functional groups. Notably, the use of aqueous ammonia as a nitrogen source eliminates the need for toxic cyanating reagents or metal catalysts, providing a green and alternative approach for the synthesis of arylacetonitriles.
Article
Chemistry, Organic
Wei Tang, Pei Fan
Summary: A nickel-catalyzed regioselective cross-electrophilic ring opening reaction of sulfonyl-protected aziridines with trifluoromethyl-substituted alkenes has been reported, providing a new and efficient entry to prepare gem-difluorobishomoallylic sulfonamides. Moreover, the scaffold of 6-fluoro-1,2,3,4-tetrahydropyridine can be constructed starting from the ring opening products via NaH-mediated intramolecular defluorinative nucleophilic vinylic substitution.
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A simple and efficient metal-free approach was developed for synthesizing 4-thio-substituted chroman and diarylmethyl thioethers, providing good yields and tolerance for labile functional groups. This method is applicable to large-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A metal-free approach to synthesize 4-thio-substituted chromans and diarylmethyl thioethers from sulfonyl hydrazones was developed. This protocol provides a straightforward route to diarylmethane derivatives with good yields. It is operationally simple and allows for the incorporation of labile functional groups, making it suitable for the synthesis of biologically relevant chemical libraries.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Wei, Lihao Liao, Tian Qin, Xiaodan Zhao
Article
Chemistry, Multidisciplinary
Yaoyu Liang, Jieying Ji, Xiaoyan Zhang, Quanbin Jiang, Jie Luo, Xiaodan Zhao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Lihao Liao, Rui An, Huimin Li, Yang Xu, Jin-Ji Wu, Xiaodan Zhao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Physical
Yuanyuan Zhang, Yaoyu Liang, Xiaodan Zhao
Summary: The enantioselective electrophilic three-component thioarylation of alkenes using chiral selenide catalysis with free phenols as arylating sources has been disclosed. Various chiral phenols were obtained in high regio-, enantio-, and diastereoselectivities. Mechanistic studies showed that the transformation proceeded through carbon nucleophilic attack to give the products rather than the intramolecular rearrangement of phenolic ether intermediates.
Article
Chemistry, Organic
Lihao Liao, Xiaodan Zhao
Summary: This paper highlights recent advances in organoselenium catalysis, including functionalization of alkenes, alkynes, and arenes through various types of selenium catalysis. These achievements are expected to inspire and benefit future research in this area.
Article
Chemistry, Multidisciplinary
Fei-Hu Cui, Yuhui Hua, Yu-Mei Lin, Jiawei Fei, Le-Han Gao, Xiaodan Zhao, Haiping Xia
Summary: The design of organometallic catalysts plays a crucial role in the development of catalytic reactions. In this study, a heterometallic [Os-Cu] complex with characteristics of bimetallics, metal-laaromatics, and pincer complexes is described as a highly effective catalyst for selective amino- and oxyselenation of unactivated alkenes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Quanbin Jiang, Huimin Li, Xiaodan Zhao
Summary: An efficient approach for catalytic electrophilic thiocarbocyclization of allenes to synthesize indene-based sulfides with excellent regioselectivities was disclosed. The reactions were conducted at low temperatures using selenide catalysis in the presence of TMSOTf. Both electrophilic arylthio and alkylthio reagents showed good performance under these conditions, and the method was also applicable to intermolecular azidothiolation of allenes.
Article
Chemistry, Organic
Wei Wei, Xiaodan Zhao
Summary: The carbon-carbon bond-forming cross-dehydrogenative coupling reaction using organoselenium catalysis involving a high-valent para-methoxyphenyl selenium species has been developed. This method enables the synthesis of alpha,alpha-disubstituted alpha-amino acid derivatives with excellent regioselectivities through vinyl or allylic C-H functionalization. The generality of this method has been demonstrated by the cross-coupling of an alkene with an oxindole and the direct functionalization of electron-rich arenes with azlactones.
Review
Chemistry, Multidisciplinary
Lihao Liao, Xiaodan Zhao
Summary: Asymmetric electrophilic reactions provide an ideal method for constructing chiral molecules, but there are many limitations. We have developed a series of chiral catalysts based on indane scaffold, which have been successfully used in various asymmetric electrophilic reactions, expanding the scope of electrophilic reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Lihao Liao, Xinru Xu, Jieying Ji, Xiaodan Zhao
Summary: In this study, an efficient catalytic asymmetric intermolecular iodinative difunctionalization reaction was reported, which successfully transformed challenging substrates into a variety of iodine-functionalized chiral molecules with excellent control over enantio- and diastereoselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yaoyu Liang, Hui Jiao, Hang Zhang, You-Qing Wang, Xiaodan Zhao
Summary: A new strategy for the construction of chiral sulfides by catalytic enantioselective hydrothiolation of alkenes via an electrophilic pathway has been developed. The superior construction of chiral thiiranium ion intermediate is the key to achieving such a transformation.
Article
Chemistry, Organic
Tian Qin, Quanbin Jiang, Jieying Ji, Jie Luo, Xiaodan Zhao
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
