Article
Chemistry, Organic
Huicong Xing, Meijuan Chen, Dong Zhang, Zhishuai Geng, Peizhong Xie, Teck-Peng Loh
Summary: A transition-metal-free catalytic system was developed for the dehydrative cross-coupling of unactivated primary/secondary alcohols with amines/amides, achieving the cleavage of C-OH bond and formation of C-N bond under environmentally benign conditions.
Article
Chemistry, Organic
Xinying Cai, Huicong Xing, Ju Qiu, Bowen Li, Peizhong Xie
Summary: A cooperative catalytic system was designed and successfully applied to the dehydrative allylation of alkenes, with a novel C-OH bond cleavage method playing a crucial role. Various alkenes and allylic alcohols with diverse functional groups can be efficiently incorporated into the desired cross-coupling reaction, yielding 1,4-dienes with moderate to high yields and high selectivity.
Article
Chemistry, Applied
Augustin Nouaille, Xavier Pannecoucke, Thomas Poisson, Samuel Couve-Bonnaire
Summary: This study presents an efficient ruthenium-catalyzed CM reaction method, successfully allowing various alkenes to react with methyl 2-fluoroacrylate to obtain trisubstituted fluoroalkenes for the first time. Additionally, an unprecedented TON value for the CM reaction involving fluoroalkenes was achieved, demonstrating good tolerance and effectiveness with a wide range of olefin partners.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Kenta Mori, Midori Akiyama, Ko Inada, Yutaka Imamura, Yuichiro Ishibashi, Yusuke Takahira, Kyoko Nozaki, Takashi Okazoe
Summary: By introducing a seven-membered N-heterocyclic carbene (NHC) ligand, a significant increase in catalyst turnover number (TON) was achieved in the cross-metathesis of tetrafluoro-ethylene (TFE) and vinyl ethers. This study provides a new approach to enhance catalytic efficiency in such reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Thien Phuc Le, Shinji Tanaka, Masahiro Yoshimura, Kazuhiko Sato, Masato Kitamura
Summary: The authors report a mixed catalytic system consisting of Pd and Ru complexes for the asymmetric dehydrative condensation between cinnamyl-type allylic alcohols and beta-keto esters. The reaction proceeds under nearly neutral conditions, resulting in high regio-, diastereo-, and enantioselective α-mono-substituted products.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Matthew S. Teynor, Windsor Scott, Daniel H. Ess
Summary: Au and Pd complexes are efficient catalysts for constructing heterocycles through pi-bond cyclization. The dynamics of pi-addition, proton transfer, and water elimination are metal-dependent, with Au skipping the alkyl intermediate dynamically while Pd may or may not skip it based on the potential energy landscape shape. Understanding catalytic intermediates and mechanisms requires atomic momentum through dynamics simulations.
Article
Chemistry, Applied
Yunjeong Park, Ji Sun Lee, Jae-Sang Ryu
Summary: An efficient synthesis protocol for cyclic sulfamidates has been developed, featuring good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li
Summary: In this study, gold- and iridium-catalyzed alkynylamide cyclization/asymmetric allylic benzylation cascade reactions were developed. Enantioenriched oxazole derivatives with a benzylic stereogenic center were obtained in good yields and high enantioselectivities. The general procedure involves the preparation of a chiral iridium complex solution, followed by the addition of reactants and catalyst. The reaction mixture is stirred at 40 degrees C until completion and the product is purified.
ACTA CHIMICA SINICA
(2023)
Article
Chemistry, Multidisciplinary
Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: This study describes the asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones. The cascade reaction involves an initial anti-Michael hydroarylation and a subsequent Nazarov cyclization. Excellent enantiomeric ratios and chemical yields are achieved under mild reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Julian Baars, Isabelle Grimm, Dirk Blunk, Joerg-Martin Neudoerfl, Hans-Guenther Schmalz
Summary: A 12-step total synthesis of the natural product dysiherbol A was achieved, revealing the need for revision of the originally proposed structure and absolute configuration. The synthesis involved key steps including Cu-catalyzed addition/enolate-trapping, Au-catalyzed double cyclization, and late installation of the C5-bridgehead methyl group. Spectroscopic measurements confirmed the identity of the synthetic compound with the natural product but with an opposite molecular rotation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Wen Zhang, Ming-Hui Zhu, Hai-Xiang Zeng, Qi-Yang Li, Wen-Bo Liu
Summary: This study presents a highly enantioselective NiH-catalyzed hydrocyclization of alkynones, yielding an array of enantioenriched heterocyclic tertiary allylic alcohols. The choice of precatalysts significantly influences the selectivity of the products, with yields reaching up to 81%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Cai-Yun Yang, De-Run Zhang, Lin-Ping Hu, Xia Li, Shi-Chen Yang, Bo Liu, Guo-Li Huang
Summary: A metal-free and oxidant-free procedure is described for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature. The transformation has high yields (up to 92%), excellent stereoselectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Mechanistic studies indicate that a sulfonyl radical pathway is involved in this reaction.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Jing Yu, Xiaoyu Yan, Feng Liu, Ying Zhou, Wenxin Man, Xiantao Ma
Summary: A mild Pd-catalyzed Tsuji-Trost reaction of allylic alcohols with an amine nucleophile in water media was developed, allowing for the green synthesis of valuable allylic amines. This new method eliminates the need for chemical activators and complex soluble ligands, and can be easily scaled up to gram scale, making it applicable for the synthesis of Naftifine, a best-selling antifungal drug, showcasing the practical significance of this method.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Min Jin, Congyun Tang, Yingying Li, Shuai Yang, Ying-Tao Yang, Lin Peng, Xiao-Nian Li, Wenjing Zhang, Zhili Zuo, Fabien Gagosz, Liang-Liang Wang
Summary: In this study, the authors present a catalytic asymmetric inverse-electron-demand-hetero-Diels-Alder reaction between neutral alkenes and alpha, beta-unsaturated ketones or aldehydes using a chiral phosphoric acid catalyst. This complex transformation allows for the formation of chiral fused heterocycles containing a central tetrahydropyran ring with high regio-, diastereo- and enantioselectivity. The stereocontrol achieved in this process is attributed to a key remote double hydrogen atom bonding interaction between the linear substrate and the catalyst.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zixuan Tong, Philip J. Smith, Helena D. Pickford, Kirsten E. Christensen, Edward A. Anderson
Summary: The study reports a gold-catalyzed reaction that allows the synthesis of polysubstituted diaminopyrroles under mild conditions. The reaction involves the formation and cyclization of an alpha-imino gold Fischer carbene, representing a new type of gold carbene intermediate.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
