Article
Chemistry, Organic
Hao Zeng, Xiaojie Fang, Zhiyi Yang, Chuanle Zhu, Huanfeng Jiang
Summary: A general and practical method for the synthesis of 5-trifluoromethylpyrazoles has been reported, using a coupling reaction between hydrazonyl chlorides and the industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP). This catalyst-free [3 + 2] cycloaddition shows high regioselectivity, mild conditions, high yields, scalability, broad substrate scope, and tolerance for various functional groups, with application in synthesizing key intermediates for an active agonist of sphingosine 1-phosphate receptor.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Leonie O'Sullivan, Ketul V. Patel, Ben C. Rowley, Duncan K. Brownsey, Evgueni Gorobets, Benjamin S. Gelfand, Jeffrey F. Van Humbeck, Darren J. Derksen
Summary: A regioselective route to C3-hydroxyarylated pyrazoles was developed using mild conditions, allowing for the synthesis of a JAK 1/2 inhibitor in just 4 steps from commercially available starting materials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Katie Ruffell, Frances R. Smith, Michael T. Green, Simon M. Nicolle, Martyn Inman, William Lewis, Christopher J. Hayes, Christopher J. Moody
Summary: Diazophosphonates, prepared from alpha-ketophosphonates by oxidation, are useful reagents in 1,3-dipolar cycloaddition reactions for synthesizing N-H pyrazoles. They possess stable properties compared to less stable diazoalkanes, and can migrate during the cycloaddition process.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Lingxiang Lu, Yi Wang, Wendy Zhang, Wen Zhang, Kimberly A. See, Song Lin
Summary: The cross-electrophile dialkylation of alkenes allows for regioselective dialkylation of alkenes without the use of transition-metal catalysts, leading to the formation of two C-(sp(3))-C-(sp(3)) bonds. This method provides a modular and efficient approach to building structural complexity in organic synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Maria E. Filkina, Daria N. Baray, Elena K. Beloglazkina, Yuri K. Grishin, Vitaly A. Roznyatovsky, Maxim E. Kukushkin
Summary: In this study, a highly regioselective synthesis of spiro-pyrazoline-imidazolidine-2,4-diones was proposed based on a 1,3-dipolar cycloaddition reaction. Regardless of whether the aryl substituents on the nitrile imine were electron donors or acceptors, the cycloaddition proceeded with high regioselectivity towards the exocyclic C=C double bond of the 5-methylidene-hydantoin. The observed regioselectivity was rationalized using DFT calculations.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Xinyu Chen, Hongqiang Liu, Hui Gao, Pinhua Li, Tao Miao, Hongji Li
Summary: An electrochemical cross-dehydrogenative coupling of indoles with xanthenes has been achieved at room temperature without the need for any catalyst or external oxidant, yielding moderate amounts of indole derivatives. Mechanistic experiments suggest a possible involvement of a radical pathway in this reaction system.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rajesh Raju, Raghavachary Raghunathan, Natarajan Arumugam, Abdulrahman Almansour, Raju Suresh Kumar, Saied M. Soliman
Summary: In this study, a regio- and diastereoselective synthesis of structurally intriguing novel hybrid heterocycles was achieved, offering a facile entry to biologically relevant classes of spiro heterocyclic hybrids.
Article
Chemistry, Organic
Bin Li, Jiang-Ling Shi, Ying Xia
Summary: The construction of all-carbon quaternary centers in small-ring systems is an important yet challenging task in organic synthesis. In this study, we developed a practical method for building all-carbon quaternary centers in gem-difluorinated cyclopropanes (DFCs) by utilizing gem-difluorocyclopropyl bromides (DFCBs) as general and versatile building blocks. The reaction involves the participation of a gem-difluorocyclopropyl radical intermediate, which undergoes coupling with a wide range of nucleophiles under copper catalysis.
Article
Chemistry, Organic
Bin Li, Jiang-Ling Shi, Ying Xia
Summary: In this study, a practical method for building all-carbon quaternary centers in gem-difluorinated cyclopropanes was developed using gem-difluorocyclopropyl bromides as a general building block. The reaction involves the participation of a gem-difluorocyclopropyl radical intermediate, which can undergo coupling with a wide range of nucleophiles under copper catalysis.
Article
Chemistry, Organic
Tingting Yan, Kaki Raveendra Babu, Yong Wu, Yang Li, Yuhai Tang, Silong Xu
Summary: A phosphine-catalyzed olefinic cross-coupling reaction between benzyl halides and fumarates has been described, providing trisubstituted alkenes with good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Article
Chemistry, Organic
Quan Gou, Qianhua Zhu, Mengjiao Deng, Weiwei Li, Xing Ran, Jianfeng Xie, Huisheng Huang, Xiaoping Tan, Minghong Zhu
Summary: The first catalytic protocol for regioselective [3 + 2] annulation of N-methyl pyridinium ylides with alkenes to establish valuable 3-unsubstituted indolizine derivatives is achieved through palladium catalysis at the unactivated position. The reaction demonstrates a wide substrate scope and excellent functional group tolerance, delivering the corresponding annulation products in good to excellent yields. The gram-scale preparation and versatile derivatization further highlight the potential of this catalytic system. Combined computational and experimental studies support the proposed reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yongxing Zhao, Rui Li, Qingzheng Zhao, Jinzhong Yao, Maozhong Miao
Summary: Unprecedented dimerizations of 2H-azirines have been achieved through the catalysis of palladium and silver. By altering the reaction conditions, fully aryl-substituted pyrrole and pyrimidine derivatives were obtained with moderate yields and regiospecificity. Control experiments demonstrated distinct catalytic effects of the two transition metals, and the proposed catalytic cycles provided plausible explanations for the chemodivergence and regioselectivity.
Article
Chemistry, Multidisciplinary
Madavi S. Prasad, Sankar Bharani, Syed Mastan Sharief, Mudavath Ravi, Murugesan Sivaprakash, Biplob Borah, L. Raju Chowhan
Summary: The application of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-dione as an activated olefin source in the DABCO-catalyzed [3 + 2] cycloaddition with N-2,2,2-trifluoroethylisatin ketimines has been disclosed. This highly efficient 1,3-dipolar cycloaddition reaction offers a variety of trifluoromethyl group bearing spiro-pyrrolidine linked oxindoles with four consecutive stereocentres in good to excellent yield and excellent diastereoselectivity.
Article
Chemistry, Physical
Zuxiao Zhang, Duong T. Ngo, David A. Nagib
Summary: A dual catalytic strategy involving an Ir photocatalyst and a Cu complex enables regioselective amination and cross-coupling of allyl alcohols with various nucleophiles. This approach allows for the formation of N-radicals via an energy transfer mechanism followed by interception of alkyl radicals for radical amino-functionalizations of olefins. Insights into the nature of Cu-based radical interception are provided through stereo, regio, and kinetic probes.
Article
Biochemistry & Molecular Biology
Yongchao Wang, Lijun Yan, Yuxin Yan, Sujin Li, Hongying Lu, Jia Liu, Jianwei Dong
Summary: In this study, a sustainable, catalysis-free, and dipolarophile-controlled three-component 1,3-dipolar cycloaddition reaction was used to synthesize 40 functionalized N-fused pyrrolidinyl spirooxindoles with excellent diastereoselectivities. The scaffolds of these compounds can be controlled by using different 1,4-enedione derivatives as dipolarophiles in EtOH at room temperature. This study provides an efficient strategy for the synthesis of natural-like and potentially bioactive N-fused pyrrolidinyl spirooxindoles.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Jung Hwan Park, Hyunik Shin, Doo Han Park, Sang-gi Lee
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2010)
Article
Chemistry, Multidisciplinary
Man-Young Yoon, Hee Bong Lee, Hyunik Shin
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2011)
Article
Chemistry, Organic
Yu Sung Chun, Ka Yeon Ryu, Young Ok Ko, Joo Yeon Hong, Jongki Hong, Hyunik Shin, Sang-gi Lee
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Organic
Ju Hyun Kim, Hyunik Shin, Sang-gi Lee
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Young Ok Ko, Yu Sung Chun, Cho-Long Park, Youngmee Kim, Hyunik Shin, Sungho Ahn, Jongki Hong, Sang-gi Lee
ORGANIC & BIOMOLECULAR CHEMISTRY
(2009)
Article
Chemistry, Organic
Yu Sung Chun, Ka Yeon Ryu, Ju Hyun Kim, Hyunik Shin, Sang-gi Lee
ORGANIC & BIOMOLECULAR CHEMISTRY
(2011)
Article
Chemistry, Organic
Yu Sung Chun, Young Ok Ko, Hyunik Shin, Sang-gi Lee
Article
Chemistry, Organic
Sam Sik Kim, Bo Seung Choi, Jae Hoon Lee, Ki Kon Lee, Tae Hee Lee, Young Ho Kim, Hyunk Shin
Article
Chemistry, Organic
Ju Hyun Kim, Yu Sung Chun, Hyunik Shin, Sang-gi Lee
SYNTHESIS-STUTTGART
(2012)
Article
Chemistry, Organic
Bong Chan Kim, Aeri Park, Ji Eun An, Won Koo Lee, Hee Bong Lee, Hyunik Shin
SYNTHESIS-STUTTGART
(2012)
Article
Chemistry, Organic
Young Ok Ko, Yu Sung Chun, Youngmee Kim, Sung Jin Kim, Hyunik Shin, Sang-gi Lee
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Organic
Yujin Oh, Jihong Lee, Hyunik Shin, Jeong-Hun Sohn
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Applied
Seung Jong Lee, Hyung Wook Moon, Kee-Young Lee, Chang Young Oh, U. Bin Kim, Hyunik Shin
Summary: A highly convergent, gram-scale synthesis of vitamin D3 analogue tacalcitol 1 is achieved through optimized reaction steps and a synthetic route, starting from simple starting materials. This method allows for efficient and scalable synthesis of a complex vitamin D3 analogue.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Jay Hyok Chang, Do Hyun Nam, Hyunik Shin
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2008)