Article
Chemistry, Organic
Hai-Xiang Zeng, Xiao-Wen Zhang, Qi-Yang Li, Wen-Bo Liu
Summary: An enantioselective Ni-catalyzed syn-hydrocyclization reaction was developed for the synthesis of α-hydroxy γ-lactams. By using Ni(OTs)(2)·6H(2)O/(S,S)-Me-Duphos as a precatalyst and (EtO)2MeSiH as a hydride source, a wide range of enantioenriched γ-lactams with fully substituted stereogenic centers were obtained in 32-84% yields with 87.5:12.5-97:3 er. This research provides a regioselective functionalization of alkynes and offers an efficient strategy for accessing functional group-enriched chiral heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Teng Ma, Xiao Li, Yuanyuan Ping, Wangqing Kong
Summary: A nickel-catalyzed three-component defluorinative reductive cross-coupling reaction for the synthesis of functionalized gem-difluoroalkenes is reported.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Jian Xiao, Ya-Wen Wang, Zhong-Ping Qiu, Yu Peng
Summary: The facile access to the tetracyclic skeleton of podophyllotoxin, a medicinally important lignan natural product, was efficiently achieved via a unique intramolecular alkylarylation of the tethered alkene in a dihalide under mild conditions using reductive nickel catalysis.
Article
Chemistry, Multidisciplinary
Johannes Klett, Lukasz Wozniak, Nicolai Cramer
Summary: 1,3,2-Diazaphospholenes hydrides (DAP-Hs) are highly nucleophilic organic hydrides that serve as main-group catalysts for a wide range of transformations, including a reductive radical cyclization of aryl and alkyl halides. Under mild conditions, the DAP catalyst undergoes a turnover process through a sigma-bond metathesis reaction with HBpin, and visible light irradiation accelerates the reaction. Mechanistic investigations suggest that visible light leads to the formation of DAP dimers, which accelerate the cyclization reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Juan C. Nieto-Carmona, Ines Manjon-Mata, M. Teresa Quiros, Gema Caballero-Santiago, Fernando Perez-Maseda, Diego J. Cardenas
Summary: In this study, we report the Ni-catalyzed cycloisomerization of 1,5-allenynes, which can yield different products depending on the substrates used. Internal alkynes can form fused bicyclic compounds, while those with terminal alkynes can generate cyclopentene derivatives. The mechanism of the reaction was also investigated and a catalytic cycle involving Ni(0)-Ni(II) species was proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Zhiyang Lin, Youxiang Jin, Weitao Hu, Chuan Wang
Summary: The nickel-catalyzed asymmetric reductive aryl-allylation reaction described in this study shows high stereo-selectivity in the synthesis of chiral compounds containing homoallyl substitution.
Article
Chemistry, Multidisciplinary
Shashank P. Sancheti, Yukta Singh, Manoj V. Mane, Nitin T. Patil
Summary: This study reports the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/pi-activation pathway, which is different from the migratory insertion/cis-trans isomerization pathway observed in other transition metal catalysis. Mechanistic investigations including experiments, NMR studies, HR-MSMS analyses, and DFT calculations provide strong support for the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Jichao Xiao, John Montgomery
Summary: A simple procedure for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes is reported. The protocol exhibits broad substrate scope, mild conditions, and a simple catalytic setup.
Article
Chemistry, Multidisciplinary
J. Caleb Hethcox, Heather C. Johnson, Jungchul Kim, Xiao Wang, Lili Cheng, Yang Cao, Melissa Tan, Daniel A. DiRocco, Yining Ji
Summary: The development and mechanistic investigation of a nickel-catalyzed sulfonylation of aryl bromides is described. The reaction demonstrates good yields with various substrates using an inexpensive and odorless inorganic sulfur salt (K2S2O5) as an effective SO2 substitute. The synthesized and characterized oxidative addition complex plays a crucial role in the reaction, with SO2 insertion likely occurring via dissolved SO2 released through thermal decomposition of K2S2O5. The use of K2S2O5 as a slow-release reservoir prevents catalyst poisoning.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Joachim Loup, Egor M. Larin, Mark Lautens
Summary: A reductive cyclization using ortho-vinylanilides for preparing N-heterocycles was catalyzed by an inexpensive and bench-stable iron complex at ambient temperature. The reaction likely involves hydromagnesiation of the vinyl group and trapping of the generated benzylic anion by an intramolecular electrophile. This method showed broad applicability in synthesizing substituted indoles, oxindoles, and tetrahydrobenzoazepinoindolone derivatives, with mechanistic studies revealing the reversibility of the hydride transfer step. The synthetic utility was further demonstrated by the formal synthesis of a bioactive compound and a group of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zhengtian Ding, Yiming Wang, Wenfeng Liu, Yate Chen, Wangqing Kong
Summary: The study presents an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from readily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, demonstrating excellent regio-, enantio-, and diastereoselectivity with a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang
Summary: In this study, a cross-electrophile strategy was successfully applied to synthesize multisubstituted allenes. Nickel-catalyzed reductive cross-coupling between propargyl carbonates and organoiodides provided a method to prepare tri- or tetrasubstituted allenes without the need for pregenerated organometallics. Furthermore, propargyl carbonates were found to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation, leading to the formation of chiral benzene-fused cyclic compounds with a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.
Article
Chemistry, Multidisciplinary
Sagar R. Mudshinge, Yuhao Yang, Bo Xu, Gerald B. Hammond, Zhichao Lu
Summary: The first C-SCF3/SeCF3 cross-coupling reactions using gold redox catalysis are reported. The new method enables the one-stop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers, with a broad substrate scope. It is scalable and can be applied to late-stage functionalization of bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yin-Xia Wang, Feng-Ping Zhang, Hao Chen, Yue Li, Jiang-Fei Li, Mengchun Ye
Summary: In this study, enantioselective Ni-catalyzed aliphatic C(sp(3))-H activation of formamides was achieved using a phosphine oxide-ligated Ni-Al bimetallic catalyst, providing a series of chiral N-containing heterocycles in yields of 40-95% and ee values of 70-95%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Luping Liu, Hyejin Kim, Youwei Xie, Christophe Fares, Philip S. J. Kaib, Richard Goddard, Benjamin List
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Hyejin Kim, Taehoon Kim, Dong Gil Lee, Sang Weon Roh, Chulbom Lee
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Prashant Chakrasali, Kyuneun Kim, Young-Sik Jung, Hyejin Kim, Soo Bong Han
Article
Multidisciplinary Sciences
Hyejin Kim, Gabriela Gerosa, Jonas Aronow, Pinar Kasaplar, Jie Ouyang, Julia B. Lingnau, Paul Guerry, Christophe Fares, Benjamin List
NATURE COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Francesca Mandrelli, Aurelie Blond, Thomas James, Hyejin Kim, Benjamin List
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Medicinal
Yeon Hee Lee, Hyeon-Min Cha, Jun Yeon Hwang, So Yeong Park, Avinash G. Vishakantegowda, Ali Imran, Joo-Youn Lee, Yoon-Sun Yi, Sangmi Jun, Ga Hyeon Kim, Hyo Jin Kang, Sang J. Chung, Meehyein Kim, Hyejin Kim, Soo Bong Han
Summary: Novel synthesized compounds show potential therapeutic applicability against HBV, providing a new avenue for safe and effective treatments for HBV infection. Investigations targeting the encapsidation of the nuclear capsid protein offer a new perspective for developing treatments against HBV infection.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Review
Biochemistry & Molecular Biology
Hyejin Kim, Chunkyu Ko, Joo-Youn Lee, Meehyein Kim
Summary: Hepatitis B virus is a major cause of human hepatitis, and compounds known as capsid assembly modulators have shown promise in disrupting virus capsid construction and life cycle. Both classical and newly identified non-classical CAMs are being studied for antiviral efficacy, with most compounds progressing to phase 2 clinical trials either alone or in combination with other drugs. The next-generation CAMs are expected to be promising candidates for extended human clinical trials based on early evaluations.
Article
Biochemistry & Molecular Biology
Hee Ra Jung, Seongman Jo, Min Jae Jeon, Hyelim Lee, Yeonjeong Chu, Jeehee Lee, Eunha Kim, Gyu Yong Song, Cheulhee Jung, Hyejin Kim, Sanghee Lee
Summary: In this study, a new chemical compound, KAS-08, was identified as an effective STING pathway activator in cancer immunotherapy. The activation of STING was achieved through direct binding or enhanced phosphorylation of STING and downstream effectors.
Article
Chemistry, Medicinal
Min Jae Jeon, Hyelim Lee, Jeehee Lee, Soo Yeon Baek, Donghee Lee, Seongman Jo, Joo-Youn Lee, Miso Kang, Hee Ra Jung, Soo Bong Han, Nam-Jung Kim, Sanghee Lee, Hyejin Kim
Summary: Stimulator of interferon genes (STING) is an endoplasmic reticulum membrane protein that plays important roles in cancer immunotherapy. Researchers have synthesized and characterized STING modulators that stimulate downstream signaling and promote immune responses, suggesting their therapeutic potential for cancer treatment.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Microbiology
Kyungseob Noh, Eun Ju Jeong, Timothy An, Jin Soo Shin, Hyejin Kim, Soo Bong Han, Meehyein Kim
Summary: This study investigated the use of a TLR7/8 agonist, compound 31, as an adjuvant to enhance the immune response to an inactivated influenza A virus vaccine. The results showed that compound 31 not only increased the production of virus-specific antibodies but also effectively neutralized the influenza A virus. In addition, the combination of compound 31 and the vaccine reduced viral infection-mediated weight loss and improved survival rates in a virus-challenge model. These findings suggest that compound 31 has potential as a mucosal vaccine adjuvant for respiratory RNA viruses.
JOURNAL OF MICROBIOLOGY
(2022)
