Article
Chemistry, Organic
Kazuki Matsuo, Eiji Yamaguchi, Akichika Itoh
Summary: This study investigates the photoinduced C-X borylation reaction of aryl halides via the formation of a halogen-bonding (XB) complex using 2-naphthol as an XB acceptor. The method is chemoselective and tolerant to a broad range of functional groups, providing a concise route to corresponding boronate esters. Mechanistic studies reveal that the formation of the XB complex between aryl halide and naphthol acts as an electron donor-acceptor complex, generating aryl radicals through photoinduced electron transfer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Man Ho Tse, Rong-Lin Zhong, Fuk Yee Kwong
Summary: In this study, a general Pd-catalyzed Miyaura borylation of sterically hindered aryl chlorides was achieved using a tailor-made phosphine ligand. The success of this reaction demonstrated the possibility of coupling highly sterically congested electrophilic partners and showed good functional group compatibility. The ligand-enabled C-B bond formation could provide fundamental knowledge for developing catalyst systems suitable for other highly sterically hindered cross-coupling reactions.
Article
Chemistry, Organic
Jee Eun Hong, Yeonghun Jung, Dahye Min, Minji Jang, Soomin Kim, Jiyong Park, Yohan Park
Summary: We report a regioselective visible-light-induced organophotoredox catalytic difunctionalization method for preparing beta-hydroxysulfides using aryl alkenes and aryl thiols. The reaction offers a wide substrate scope and high yields by combining experimental and computational studies. The method provides a platform for deriving various beta-hydroxysulfides containing aromatic elements, which are biologically important.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuanyuan An, Xiaolong Li, Shuangshuang Xia, Yongchan Jian, Fei Wen, Zhenyu Liu, Jiaying He, Yali Shen, Yubin Wang
Summary: In this study, a regioselective hydroborylation of ketene dithioacetals with NHC-borane was achieved under mild conditions via a visible-light-promoted radical chain process. This method features good functional group tolerance, a relatively broad substrate scope, and good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Mo Yu, Kaikai Niu, Ziwen Wang, Yuxiu Liu, Qingmin Wang
Summary: This study presents a protocol for visible-light-induced perfluoroalkylation reactions of aryl acrylic acids, which is important for late-stage modification of biologically active molecules. The reactions proceed in a decarboxylative manner using perfluoroalkyl iodides as radical precursors and inexpensive eosin Y as a photocatalyst. The easy accessibility of perfluoroalkyl iodides and the broad substrate scope, mild conditions, and metal-free catalyst make this protocol applicable for transforming inexpensive raw materials to high-value chemicals.
Article
Chemistry, Organic
Boyu Yan, Yutong Zhou, Jieliang Wu, Maogang Ran, Huihui Li, Qiuli Yao
Summary: The study presents a simple and catalyst-free photochemical strategy for the direct reduction of aryl salts and haloarenes to arenes or deuterium-labeled arenes, confirming the formation of aryl radical intermediates.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Feng-Chen Gao, Ming Li, Heng-Yu Gu, Xin-Yi Chen, Shuang Xu, Yi Wei, Kai Hong
Summary: In this study, a visible light-induced C-H bromination reaction was developed for the synthesis of benzyl boronic esters. This method offers high yields, mild conditions, simple operation, and good functional group tolerance. Additionally, the synthesis of halogenated geminal diborons was demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yihuan Lai, Arjun Halder, Jaehwan Kim, Thomas J. Hicks, Phillip J. Milner
Summary: In this study, it was discovered that cumulenes-organic molecules with multiple consecutive double bonds-can serve as catalytic redox mediators for the electroreductive radical borylation of inert substrates (such as electron-neutral and electron-rich aryl chlorides) at relatively mild cathodic potentials (-1.9 V vs. Ag/AgCl). This finding will guide the development of other sustainable purely electroreductive radical transformations using organic redox mediators.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Liubov I. Panferova, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This study presents the removal of a tetrafluoropyridinyl group tethered to a sulfur atom using a complex of N-heterocyclic carbene (NHC) with borane. The reaction is carried out under blue light irradiation with a disulfide as a radical initiator. Selective cleavage of S-Ar bond rather than the weaker S-Alk bond is achieved through aromatic radical substitution of the thiyl group by a NHC-stabilized boron-centered radical. Alkyl thiols, the primary products of dearylation, can be in situ oxidized or alkylated to form disulfides or sulfides, respectively.
Article
Chemistry, Organic
Jorge C. Herrera-Luna, David Diaz Diaz, Alex Abramov, Susana Encinas, M. Consuelo Jimenez, Raul Perez-Ruiz
Summary: In this study, the borylation of heteroarene boronate esters was achieved under very mild conditions in an easy-to-use gel nanoreactor, using visible light as the energy source at room temperature in photocatalyst-free and aerobic conditions. The gel network provided a stabilizing microenvironment to support a wide substrate scope, making this protocol attractive for the synthesis of new materials.
Article
Chemistry, Physical
Chuan Ding, Peng-Fei Huang, Biquan Xiong, Ke-Wen Tang, Yu Liu
Summary: A new and powerful visible-light-induced difunctionalization of alkylidenecyclopropanes was developed via a ring-opening process. Acyl chlorides were used as both acyl and Cl sources. This strategy offers an effective route for the difunctionalization of the C-C bond by constructing new C-C and C-Cl bonds in one pot. It also exhibits broad substrate scope and tolerance towards various functional groups.
Article
Chemistry, Multidisciplinary
Palani Natarajan, Partigya, Pooja
Summary: A novel blue LED-induced method for synthesizing a variety of compounds has been developed without the need for a photoredox catalyst. This method offers advantages such as environmental friendliness, mild conditions, scalability, absence of toxic solvents/additives, and absence of transition metals.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Fan Gao, Wanru Xiao, Shujun Li, Bing Yu
Summary: A new organic-inorganic hybrid material has been synthesized and shown to have potential in visible-light-induced organic reactions. The material also exhibits outstanding sustainability and recyclability.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Organic
Chunbo Bo, Fei Chen, Qingqing Bu, Zhi-Hong Du, Min Li, Bin Dai, Ning Liu
Summary: A light-driven organocatalytic approach using 9,10-dibromoanthracene as a photocatalyst and N-fluorobenzenesulfonimide as an oxidant is reported for alkoxylation of the benzyl C-H bond. This reaction proceeds at room temperature and is capable of converting a variety of alkyl biphenyl and coupling partners, including a variety of alcohol and carboxylic acid, as well as peroxide, to the desired products under 400 nm light irradiation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming-Hang Bi, Ying Cheng, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study describes a selective three-component 1,4-difluoroalkylesterification enabled by dual photoredox and copper catalysis. The protocol utilizes commercially available CF2-reagents as radical precursors and carboxylic acids as oxygen-based nucleophiles, allowing access to difluoroalkylated allylic esters. Furthermore, this protocol can also be extended to intramolecular two-component 1,4-difluoroalkylesterification for the synthesis of 3-substituted benzobutyrolactones. Preliminary mechanistic studies provide evidence for a radical process.
Article
Chemistry, Multidisciplinary
Huan Yang, Li Zhang, Lei Jiao
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Li Zhang, Huan Yang, Lei Jiao
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Li Zhang, Lei Jiao
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Li Zhang, Lei Jiao
Article
Chemistry, Multidisciplinary
Li Zhang, Zhong-Qian Wu, Lei Jiao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Hao Jia, Andreas P. Haering, Florian Berger, Li Zhang, Tobias Ritter
Summary: In this study, we report the synthesis and application of a novel trifluoromethylating reagent TT-CF3+OTf-, which can be used in various trifluoromethylation reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Li Zhang, Tobias Ritter
Summary: Aromatic C-H late-stage functionalization poses challenges in terms of reactivity, selectivity, and substrate scope, but also shows potential for development. It is necessary to address current challenges and explore new strategies and directions for growth.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hui Zhou, Jung Tae Han, Nils Noethling, Monika M. Lindner, Judith Jenniches, Clemens Kuehn, Nobuya Tsuji, Li Zhang, Benjamin List
Summary: In this study, we report an organocatalytic enantioselective synthesis method for the preparation of tertiary silyl ethers with central chirality on silicon. The reaction involves a desymmetrizing carbon-carbon bond forming silicon-hydrogen exchange reaction of symmetrical bis(methallyl)silanes with phenols using newly developed catalysts. A variety of enantiopure silyl ethers were obtained in high yields with good chemo- and enantioselectivities.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Li Zhang, Jiyao Yan, Dilgam Ahmadli, Zikuan Wang, Tobias Ritter
Summary: Direct C-H fluorination is an efficient strategy to construct aromatic C-F bonds, but the presence of other functional groups and the high energy barrier of C-F bond formation make the transformation challenging. In this study, a new concept for C-H nucleophilic fluorination without the formation of azaarene Meisenheimer intermediates was reported, achieving successful nucleophilic oxidative fluorination of quinolines through an asynchronous concerted F--e(-)-H+ transfer.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Huan Yang, Li Zhang, Fei-Yu Zhou, Lei Jiao
