Article
Chemistry, Organic
Shaoqun Zhu, Yingjie Pan, Yue Sun, Xiaoyan Hong, Xiaoyun Chen, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou
Summary: In this study, a copper-catalyzed bromo-cyanomethylative cyclization of 1,6-enynes is demonstrated. The treatment of 2-bromoacetonitrile with CuI enables the generation of alkyl radicals, triggering a radical addition/cyclization/bromination sequence that yields functionalized heterocycles with vinyl C-Br bonds in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yao Ouyang, Chao-Lai Tong, Xiu-Hua Xu, Feng-Ling Qing
Summary: The first copper and zinc copromoted trifluoromethylation using trifluoromethanesulfonic anhydride (Tf2O) as a trifluoromethylating reagent has been developed, affording bromo(chloro)trifluoromethylated products in good yields. CuX2 plays a dual role as the catalyst and halide source, whereas 2,2'-bipyridine acts as both the activation reagent and ligand.
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, T. L. Chandana, Yun-Jou Wang, Jeh-Jeng Wang
Summary: Environmentally friendly acid-catalyzed ynamide N-Csp bond cleavage, alkyne migration, and stereospecific functionalization with anisole derivatives for the synthesis of challenging cis-alkene tethered indole scaffolds in a very short reaction time (5-10 min).
Article
Chemistry, Applied
Zhuangzhuang Guo, Xiaoyu Chen, Yingying Xue, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu
Summary: A copper-catalyzed cascade difunctionalization reaction has been reported, which allows for the construction of Csp(3)-CF2/C-C bonds by reacting unactivated olefins with readily available R-f-I reagents. This strategy provides a convenient access to a variety of useful perfluoroalkylated tricyclimidazole derivatives in reasonable yields. Preliminary mechanistic studies suggest that the reaction proceeds through a radical/SET pathway. The transformation offers mild conditions, simple operation, atomic economy, and a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Alisa S. Sunagatullina, Ferdinand H. Lutter, Konstantin Karaghiosoff, Paul Knochel
Summary: We have developed a new iron-catalyzed reaction for converting alkyl iodides into alkylzinc iodides. The reaction exhibits diastereoselective ring closures when a remote double bond is present at position 5. Furthermore, the resulting zinc reagents can be further reacted with various electrophiles under copper or palladium catalysis to provide diverse polyfunctional products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hong Xin, Li-Na Guo, Mingyu Yang, Cheng Guan, Zi-Hang Yuan, Xin-Hua Duan
Summary: An efficient tandem Dowd-Beckwith ring expansion/C-H functionalization of tetrahydroisoquinolines (THIQs) upon photocatalysis is reported, which provides a unique strategy to connect important medium-sized cycloalkanones with THIQ skeletons and generate all-carbon quaternary carbon centers. This protocol offers step- and atom-economy, mild reaction conditions, and good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Koyo Kazama, Rei Kurokawa, Kei Inoue, Hidenori Kinoshita, Katsukiyo Miura
Summary: One-pot synthesis of siloles from readily available starting materials was proposed. This methodology allows for the preparation of multisubstituted siloles in good to excellent yields with complete regioselectivity. Sequential reactions, including lithiation, silylation, and diisobutylaluminum-hydride-promoted cyclization, enable the efficient formation of the siloles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ming Li, Yuke Li, Wan-Yuan Jia, Guo-Qing Sun, Fan Gao, Guo-Xiao Zhao, Yi-Feng Qiu, Xi-Cun Wang, Yong-Min Liang, Zheng-Jun Quan
Summary: The free radical cyclization reaction is a promising strategy for the formation of ring frameworks. In this study, we report a copper-catalyzed tandem radical cyclization strategy for preparing substituted lactam derivatives. This reaction utilizes a radical coupling approach, allowing a wide range of alkenes and being compatible with primary, secondary, and tertiary radicals. Density functional theory calculations were also performed to gain insights into the reaction mechanism.
Article
Chemistry, Organic
Rattana Worayuthakarn, Kanyanat Boontan, Kittipong Chainok, Somsak Ruchirawat, Nopporn Thasana
Summary: An efficient divergent approach to functionalized naphthalene derivatives, the naphthalenamides, has been developed using enone-oxazolones as precursors via base-mediated and silver-catalyzed cyclization. Hydroxynaphthalenamides were constructed with good yields by C-C bond formation, oxazolone ring-opening, and aromatization using base in methanol with heating. Phosphorylated dihydronaphthylamides were generated in good yields through silver-catalyzed cyclization involving phospha-1,4-addition/intramolecular ring closure with concomitant C-P/C-C bond formation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yi Liu, Wenjing Zhu, Xiao Yu, Hongyan Liu, Zenghui Zhang, Mei Zhang, Jinbo Zhao, Yacong Wang, Chengcai Xia
Summary: A method for synthesizing dihydropyrazoles has been developed, featuring mild reaction conditions and good functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hui Shen, Yu Du, Jian Kan, Weiping Su
Summary: A palladium-catalyzed intramolecular cyclization has been developed for the synthesis of a series of 3-substituted 2-oxindoles in high yields. The method features easy to prepare starting materials, broad substrate scope, and excellent functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Shengnan Lin, Jianchao Cui, Yu Chen, Yi Li
Summary: A copper-catalyzed trifluoromethylarylated cycloaddition of imidazoles and olefins using CF3SO2Cl as the radical source was reported, leading to the synthesis of highly functionalized tricyclic imidazoles. The procedure showed a wide substrate scope with isolated yields ranging from 25% to 93% (36 examples). Mechanistic studies supported a free trifluoromethyl radical pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ganesh Chandra Upreti, Tavinder Singh, Kirti Khanna, Anand Singh
Summary: This article describes the development of excited-state palladium-catalyzed alkylative cyclization of acrylamides and the alkylation of quinoxalinones. The highlights of this reactivity manifold include the use of various unactivated alkyl halides as alkyl radical precursors and a simple catalyst system. The reactions have a wide scope, occur under mild conditions, and provide excellent yields of products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pin Ding, Lingbo Han, Jiaxing Bai, Jingjing Liu, Xinjun Luan
Summary: The study introduces an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation for assembling synthetically useful carbazoles in one step. The key to the success of this reaction lies in the careful selection of amino sources and Pd(0) catalysts.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Applied
Zheng-Jia Shen, Binbin Huang, Na Ma, Lijuan Yao, Chao Yang, Lin Guo, Wujiong Xia
Summary: A tunable electrosynthesis of sulfonyl- and bromo-substituted indolo[2,1-alpha]isoquinoline derivatives has been developed, offering valuable compounds in moderate to good yields. This reaction proceeds via a radical cascade cyclization pathway and features broad substrate scope and good functional group tolerance under transition metal-free and oxidant-free conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
K. Cory MacLeod, Fabian S. Menges, Sean F. McWilliams, Stephanie M. Craig, Brandon Mercado, Mark A. Johnson, Patrick L. Holland
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
K. Cory MacLeod, Sean F. McWilliams, Brandon Q. Mercado, Patrick L. Holland
Article
Chemistry, Multidisciplinary
Vladimir Pelmenschikov, Leland B. Gee, Hongxin Wang, K. Cory MacLeod, Sean F. McWilliams, Kazimer L. Skubi, Stephen P. Cramer, Patrick L. Holland
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Inorganic & Nuclear
Benjamin E. Olafsen, Giuseppe V. Crescenzo, Luke P. Moisey, Brian O. Patrick, Kevin M. Smith
INORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Richard A. Lewis, K. Cory MacLeod, Brandon Q. Mercado, Patrick L. Holland
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Multidisciplinary
Wen Zhou, Brian O. Patrick, Kevin M. Smith
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Inorganic & Nuclear
Thomas R. Dugan, K. Cory MacLeod, William W. Brennessel, Patrick L. Holland
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2013)
Article
Chemistry, Inorganic & Nuclear
Wen Zhou, Addison N. Desnoyer, James A. Bailey, Brian O. Patrick, Kevin M. Smith
INORGANIC CHEMISTRY
(2013)
Article
Chemistry, Inorganic & Nuclear
Thomas R. Dugan, Eckhard Bill, K. Cory MacLeod, William W. Brennessel, Patrick L. Holland
INORGANIC CHEMISTRY
(2014)
Article
Chemistry, Multidisciplinary
K. Cory MacLeod, David J. Vinyard, Patrick L. Holland
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Multidisciplinary
K. Cory MacLeod, Patrick L. Holland
Article
Chemistry, Inorganic & Nuclear
K. Cory MacLeod, Ida M. DiMucci, Edward P. Zovinka, Sean F. Mcwilliams, Brandon Q. Mercado, Kyle M. Lancaster, Patrick L. Holland
Correction
Chemistry, Multidisciplinary
Sean F. McWilliams, Emma Brennan-Wydra, K. Cory MacLeod, Patrick L. Holland
Article
Chemistry, Multidisciplinary
Sean F. McWilliams, Emma Brennan-Wydra, K. Cory MacLeod, Patrick L. Holland
Meeting Abstract
Chemistry, Multidisciplinary
Kevin M. Smith, Wen Zhou
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)