Article
Chemistry, Multidisciplinary
Yu-Bin Wang, Fei Chen, Min Li, Qingqing Bu, Zhihong Du, Jichang Liu, Bin Dai, Ning Liu
Summary: Visible light-promoted strategies were developed for the synthesis of gem-dihaloenones using alkynes and polyhalomethanes as the starting materials. The methods produce a broad range of gem-dibromoenones and gem-dichloroenones without using photocatalysts or additives, such as bases and oxidants. This is the first example of a photocatalyst-free strategy for the photo-promoted synthesis of gem-dihaloenones. These protocols were compatible with various terminal and internal alkynes and were effective in gram-scale experiments.
Article
Chemistry, Organic
Zhi-Hao Chen, Xiao-Xuan Su, Qingjiang Li, Jia-Qiang Wu, Tian-Miao Ou, Honggen Wang
Summary: A mild and metal-free synthesis of alpha-boryl ketones has been achieved via the hydration or oxidation of N-methyliminodiacetyl boronate (B(MIDA))-decorated alkynes. The hydration of arylethynyl B(MIDA)s can be conducted at room temperature with decent functional group tolerance using a new hydration system comprised of AcCl and H2O in HFIP. Furthermore, an oxidative carbon deletion process of propargylic B(MIDA)s has been developed for the synthesis of aliphatic alpha-boryl ketones, and an intriguing beta-boron effect has been observed to account for the unique site- and chemoselectivities. The application of the products in the synthesis of borylated heterocycles has also been demonstrated.
Article
Chemistry, Multidisciplinary
Yang Zheng, Jingxing Jiang, Yue Li, Yongliang Wei, Junqi Zhang, Jundie Hu, Zhuofeng Ke, Xinfang Xu, Liming Zhang
Summary: An oxidative strategy is reported for the direct access of alpha-oxo BMIDA gold carbenes from BMIDA-terminated alkynes. These BMIDA gold carbene species can insert into various C-H bonds and undergo other reactions, leading to the formation of structurally diverse alpha-BMIDA ketones. The role of BMIDA is found to be an electron-donating group that reduces the electrophilicity of the gold carbene center, as supported by DFT studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Guanghui Wang, Ximei Zhao, Jian Jia, Zengzeng Li, Haotian Li, Yongqiang Wang
Summary: This study presents a zinc-catalyzed method for inserting vinyl carbenes generated from cyclopropenes into the B-H bonds of Lewis base-borane adducts, providing a concise and efficient route to allylboranes. The use of inexpensive and low-toxicity ZnCl2 as the catalyst allows for high-yielding allylboranes with excellent E/Z ratios. Moreover, this method offers a broader scope of Lewis base-borane adducts compared to other catalytic methods for metal carbene insertion into B-H bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guanghui Wang, Yongqiang Wang, Zengzeng Li, Haotian Li, Mingwu Yu, Maofu Pang, Ximei Zhao
Summary: The gold-catalyzed cyclization/hydroboration of 1,6-enynes provides a facile and versatile method to access bicyclo[3.1.0]hexane boranes. The stable products can undergo various transformations.
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yuan Yang, Dilver Pena Fuentes, Xiao-Feng Wu
Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article
Chemistry, Physical
Liam J. Donnelly, Teresa Faber, Carole A. Morrison, Gary S. Nichol, Stephen P. Thomas, Jason B. Love
Summary: Transition metal complexes with metal-boron bonds, particularly iridium polyboryl and polyhydrido-boryl complexes, are important catalysts for C-H borylation reactions. In this study, polyhydride boryl phosphine rhenium complexes were shown to be capable of catalyzing the C-H borylation of heteroaromatic substrates. The boryl complex derived from the rhenium complex acted as a catalyst for various heteroarenes, exhibiting similar reactivity to iridium analogues.
Article
Chemistry, Inorganic & Nuclear
Ding-Nan Shih, Ramalingam Boobalan, Yi-Hung Liu, Rong-Jie Chein, Ching-Wen Chiu
Summary: In recent years, a tricoordinate borenium ion has been studied for its applications in Lewis acid catalysis, as well as in the development of asymmetric catalysis mediated by a chiral borenium ion. Chloroborane masked borenium ions have been prepared to stabilize the electron-deficient boron atom and utilized as catalysts for enantioselective Diels-Alder cycloaddition reactions. Additionally, the stereoselectivity of the cycloaddition can be controlled and improved by the coordination of SnCl4 at the bridging chloride of the borenium ion.
INORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Ana B. Cuenca, Elena Fernandez
Summary: The boron-Wittig reaction involves the condensation of easy manageable lithium alpha-bis(boryl)carbanions with carbonyl derivatives to form metalloid-substituted alkenes, which are important building blocks for the synthesis of all-carbon substituted olefins. This reaction is stereoselective and can be applied to a variety of carbonyl derivatives, with a focus on controlling the stereochemical outcome. Its synthetic potential is demonstrated through applications to target compounds via subsequent C-C bond forming processes.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Lukas Tendera, Laura Kuehn, Todd B. Marder, Udo Radius
Summary: The synthesis of the first terminal mono-boryl complexes of nickel, without a pincer ligand, is reported. Various reactions were conducted to exchange ligands and obtain the desired nickel mono-boryl complexes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Tsuyoshi Taniguchi
Summary: Boron-centred radicals ligated by N-heterocyclic carbenes (NHCs) have shown potential in main group chemistry and synthetic chemistry due to their high stability and diverse applications; recent advances in the synthesis and reactions of NHC-boryl radicals have contributed significantly to radical chemistry, organoboron chemistry, and polymer science.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Applied
Xueer Wang, Zhongwei Feng, Wenqi Guo, Wentao Zhong, Xiaoyu Liu, Cheng Wang, Zhisheng Fu, Zhiqiang Fan
Summary: Three alpha-diimine Ni (II) catalysts were synthesized and investigated for ethylene polymerization using alkyl aluminum and organoboron compounds as binary cocatalyst. The addition of sodium tetrakis[3,5-bis (trifluoromethyl) phenyl]borate (NaBArF) improved the catalytic activity of all three catalysts, especially for Cat.3. The charging sequence of NaBArF and the [B]/[Ni] ratio had significant effects on the catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Song-Zhou Cai, Danhua Ge, Li-Wen Sun, Weidong Rao, Xin Wang, Zhi-Liang Shen, Xue-Qiang Chu
Summary: This study presents an efficient three-component tandem reaction of polyftuoroalkyl peroxides with sulfinates for constructing fluoroalkylated tetrasubstituted furan derivatives. The reaction proceeds via an unprecedented sequence, cleaving four C(sp(3))-F bonds and forming two new C-S bonds. It offers a transition metal-free C-F bond functionalization with broad substrate scope and excellent functional group tolerance.
Review
Chemistry, Multidisciplinary
Kanak Kanti Das, Somenath Mahato, Subrata Hazra, Santanu Panda
Summary: Organoboron compounds are important and versatile synthetic intermediates in the preparation of organic molecules. Among all organoboron compounds, beta-boryl carbonyl compounds have emerged as promising intermediates for various synthetic transformations. This mini-review provides an overview of the numerous racemic and asymmetric beta-borylation methods developed to date.
Article
Chemistry, Organic
Tesfaye Tebeka Simur, Tian-Yu Peng, Yi-Feng Wang, Xiu-Wei Wu, Feng-Lian Zhang
Summary: A boryl radical-promoted dehydroxylative alkylation of 3-hydroxy-oxindole derivatives is achieved by adding 4-dimethylaminopyridine (DMAP)-boryl radical to the amide carbonyl oxygen atom, inducing a spin-center shift process and promoting C-O bond cleavage. The elimination of a hydroxide anion from a free hydroxy group is also accomplished. Capture of the generated carbon radical with alkenes leads to a variety of C-3 alkylated oxindoles. This method offers a simple operation and broad substrate scope.
Article
Chemistry, Organic
Ji-Min Yang, Yan Cai, Shou-Fei Zhu, Qi-Lin Zhou
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Ji-Min Yang, Zi-Qi Li, Mao-Lin Li, Qiao He, Shou-Fei Zhu, Qi-Lin Zhou
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Organic
Qing-Qing Cheng, Ji-Min Yang, Huan Xu, Shou-Fei Zhu
Article
Chemistry, Multidisciplinary
Yue Pang, Qjao He, Zi-Qi Li, Ji-Min Yang, Jin-Han Yu, Shou-Fei Zhu, Qi-Lin Zhou
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Physical
Ming-Yao Huang, Ji-Min Yang, Yu-Tao Zhao, Shou-Fei Zhu
Article
Chemistry, Multidisciplinary
Ji-Min Yang, Feng-Kai Guo, Yu-Tao Zhao, Qiao Zhang, Ming-Yao Huang, Mao-Lin Li, Shou-Fei Zhu, Qi-Lin Zhou
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Ji-Min Yang, Yang Yu, Julius Rebek
Summary: This study utilizes cavitands to facilitate intramolecular aldol/dehydration reactions of long-chain precursors, leading to efficient macrocyclization in aqueous solution. The cavitands act as hosts for the molecular templates, resembling the role of templates in biological catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Ji-Min Yang, Yong-Qing Chen, Yang Yu, Pablo Ballester, Julius Rebek
Summary: The study reports the synthesis and characterization of two water-soluble container compounds with rigidified open ends. These compounds, with different spacers, preorganize into vase-like shapes and show good binding affinity to a variety of guests, demonstrating selectivity and adsorption properties in aqueous medium.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Hau Sun Sam Chan, Ji-Min Yang, Jin-Quan Yu
Summary: This study demonstrates the highly site-selective activation of free carboxylic acids using palladium catalysts with specific ligands, leading to the synthesis of diverse compounds and showcasing the versatility of the remaining carboxyl group in further synthetic applications.
Article
Multidisciplinary Sciences
Ji-Min Yang, Yu-Kun Lin, Tao Sheng, Liang Hu, Xin-Pei Cai, Jin-Quan Yu
Summary: Regiocontrol is challenging in traditional cycloaddition reactions between unsaturated carbon compounds. This study reports a regio-controllable synthesis of benzocyclobutenes (BCBs) through a palladium-catalyzed double C-H activation of adjacent methylene units in carboxylic acids using bidentate amide-pyridone ligands. This method allows for the synthesis of diversely functionalized BCBs and hetero-BCBs found in drug molecules and bioactive natural products.
Article
Chemistry, Multidisciplinary
Faiz-Ur Rahman, Ji-Min Yang, Yun-Hui Wan, Zhang Hui-Bin, Ioannis D. Petsalakis, Giannoula Theodorakopoulos, Julius Rebek, Yang Yu
CHEMICAL COMMUNICATIONS
(2020)
Review
Chemistry, Organic
Jimin Yang, Ziqi Li, Shoufei Zhu
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2017)
