Article
Chemistry, Multidisciplinary
Hefei Yang, Le-Cheng Wang, Yu Zhang, Dongling Zheng, Zhengkai Chen, Xiao-Feng Wu
Summary: A substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed to synthesize structurally diverse trifluoromethyl-containing indoles and indolines. The regioselectivity of the reaction is determined by the structure of the alkene substrates.
Article
Chemistry, Physical
Sangeth Jenthra, Totan Mondal, Gregor Kemper, Marcus Lantzius-Beninga, Markus Hoelscher, Walter Leitner
Summary: A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids and terminal olefins was achieved using a catalytic system composed of Pd(OAc)(2) in the presence of phosphine-sulfonamido ligands. The bulky ligand L1 favored the formation of 1,1-disubstituted branched olefins with high selectivity, while the less bulky ligand L2 resulted in the formation of 1,2-disubstituted linear products in high yield. Detailed mechanistic investigation revealed that the aryl substituent at the sulfonamide group of ligand L1 favored 1,2-insertion, while the less bulky ligand L2 favored 2,1-insertion.
Article
Chemistry, Organic
Rui Li, Chen-Xi Yang, Bai-Hua Niu, Li-Juan Li, Ji-Mei Ma, Zi-Long Li, Hong Jiang, Wan-Min Cheng
Summary: A highly efficient photoinduced nickel-catalyzed method for the C-heteroatom cross-coupling of aryl halides is reported. This method does not require external photosensitizers and can successfully couple various nucleophiles with electronically diverse aryl halides, providing a universal approach for different C-heteroatom coupling reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jorge Victoria-Miguel, William H. Garcia-Santos, Alejandro Cordero-Vargas
Summary: An efficient visible light catalyzed method for the preparation of 2,3-dihydrofurans using 2-bromoketoesters as radical precursors and alkyl enol ethers as acceptors was reported. The photoredox cycle provides an oxonium ion that is captured by an internal nucleophile to yield the corresponding dihydrofurans. The obtained products contain a versatile acetal moiety at C-2, allowing for the transformation into various heteroaromatic and nonaromatic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Kang Wu, Tian-Zhang Wang, Yu-Feng Liang
Summary: This nickel-catalyzed reductive cross coupling reaction allows for the efficient generation of structurally diverse thioesters by activating carboxylic acids with disulfides. The reaction demonstrates broad substrate scope and wide functional group tolerance, making it a convenient and practical tactic for constructing carbon-sulfur bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Xiao-Di Nie, Xiao-Li Han, Jian-Ting Sun, Chang-Mei Si, Bang-Guo Wei, Guo-Qiang Lin
Summary: This study introduces a novel method for the Ni(OTf)(2)-catalyzed hydroamination of ynamides with secondary amines, demonstrating high yields and excellent regioselectivity. The protocol shows good functional group tolerance for ynamides and a broad substrate scope of secondary aryl amines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
Zhilong Li, Chengyang Li, Yu Ding, Haohua Huo
Summary: The merger of nickel catalysis and photocatalysis has provided a transformative platform for the rapid assembly of molecular complexity. However, the development of enantioselective transformations in nickel photoredox catalysis remains challenging but holds great promise.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Organic
Kwan Hong Min, Naeem Iqbal, Eun Jin Cho
Summary: By utilizing a rare bidentate primary aminophosphine ligand, a nickel-catalyzed reductive coupling of alkynes and amides was achieved, leading to the synthesis of highly functionalized indoles containing trifluoromethyl groups, which is of significance in drug research.
Review
Chemistry, Physical
Kuai Wang, Wangqing Kong
Summary: Organofluorine compounds have received significant attention in various industries due to their unique chemical and physical properties. However, the synthesis of these compounds still faces challenges, including difficulties in handling fluorinating reagents and controlling chemoselectivity. In recent decades, the development of Nickel-catalyzed defluorinative cross-couplings has provided powerful strategies for the construction of fluorinated organic compounds. This review summarizes important advances in this field, focusing on aryl fluorides, gem-difluorovinyl, and trifluoromethyl compounds.
Article
Chemistry, Multidisciplinary
Jinglin Qu, Zijuan Yan, Xuchao Wang, Jun Deng, Feipeng Liu, Zi-Qiang Rong
Summary: Aryl ketones, an important class of organic compounds, are widely used in the synthesis of pharmaceuticals, biologically active molecules, and functional materials. This study presents a facile synthetic method for the construction of aryl ketones through Ni-catalyzed cross coupling of epoxides with aryltriflates, resulting in highly regioselective conversion with good yields in a redox neutral manner.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Pengbo Zhang, Guo Yu, Wenwu Li, Zhigang Shu, Longyu Wang, Zhaoting Li, Xia Gao
Summary: An unprecedented copper-catalyzed multicomponent radical-based reaction has been developed for the direct preparation of highly functionalized CF3-containing S-alkyl phosphorothioates at room temperature. This protocol highlights its potential in late-stage functionalization of complex molecules and provides a new avenue for constructing C(sp(3))-S-P bonds.
Article
Chemistry, Multidisciplinary
Xiaomin Shu, De Zhong, Yanmei Lin, Xiao Qin, Haohua Huo
Summary: We report a general and modular approach for the direct enantioselective alpha-arylation of saturated azacycles and acyclic N-alkyl benzamides via nickel/photoredox dual catalysis. This method requires no oxidants or organometallic reagents, features broad substrate scope and high enantioselectivities, and is applicable to late-stage diversification of medicinally relevant complex molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Perla Bharath Kumar, Chittala Emmaniel Raju, Patel Hinal Chandubhai, Balasubramanian Sridhar, Galla V. Karunakar
Summary: Molecules obtained from nature have various biological applications in medicinal chemistry, agrochemicals, and material sciences. Oxygen-containing molecules such as chromenes and benzochromenes are found to have potential biological applications.
Article
Chemistry, Physical
Hongyu Wang, Chen-Fei Liu, Tong-De Tan, Kyna Ru Bin Khoo, Ming Joo Koh
Summary: The study demonstrates a new method for the highly efficient and site-selective 1,2-diarylation of aliphatic-1,3-dienes using N-heterocyclic carbene (NHC)-Ni(0) catalyst, allowing for the synthesis of products containing tertiary or quaternary centers.
