Review
Chemistry, Multidisciplinary
Kelvin Li, Darryl Fong, Eric Meichsner, Alex Adronov
Summary: Efficient reactions driving progress in synthetic chemistry focus on mild conditions, no by-products, and rapid completion. The strain-promoted azide-alkyne cycloaddition has gained popularity in organic synthesis, bioorthogonal chemistry, and polymer chemistry, leading to significant achievements in producing various polymeric constructs for diverse applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Cheng Zhao, Man-Zhen Gu, Yi-Yuan Chen, Xiao-Wei Hu, Yi-Bing Xu, Xiao-Min Lin, Xin-Ni Liu, Long Chen, Guo-Shu Chen, Yun-Lin Liu
Summary: A base-catalyzed divergent synthesis of multisubstituted imidazoles has been developed through TosMIC-based [3 + 2] cyclization reaction, resulting in different substitution patterns of products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xinyi Wan, Haiwen Li, Shan Wang, Cunde Wang
Summary: A method mediated by acetic acid was developed for the synthesis of highly stereoselective tetrahydrothiopyranols. The method is characterized by cheap and readily available starting materials, simple operation, and mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Het Vyas, Ashvin J. Gangani, Aiswarya Mini, Shengjia Lin, Jia-Min Chu, Caitlyn O. Agee, Justin Gabriel, R. Thomas Williamson, Yong Zhang, Abhishek Sharma
Summary: This study reports the development of vinyl cyclopropyl diborons (VCPDBs) as a versatile source of previously unknown homoallylic alpha,alpha-diboryl radicals via thiyl radical catalyzed diboron-directed ring opening. These diboryl stabilized radicals underwent smooth [3+2] cycloaddition with a variety of olefins to provide diboryl cyclopentanes in good to excellent diastereoselectivity. The mild reaction conditions also allowed a one-pot VCP ring-opening, cycloaddition-oxidation sequence to afford disubstituted cyclopentanones. Control experiments and DFT analysis of reaction mechanism support a radical mediated pathway and provide a rationale for the observed diastereoselectivity. To the authors' knowledge, these are the first examples of the use of geminal diboryl group as an activator of VCP ring opening and cycloaddition reaction of alpha-boryl radicals.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Rene Hommelsheim, Robin van Nahl, Lena M. Hanek, Jas S. Ward, Kari Rissanen, Carsten Bolm
Summary: This study reports a palladium-catalyzed domino reaction that enables the synthesis of 3-amino-substituted 1,2,4-benzothiadiazine 1,1-dioxides at room temperature. The method demonstrates good substrate compatibility and mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yu-Qing Xiao, Miao-Miao Li, Zheng-Xin Zhou, Yu-Jie Li, Meng-Yue Cao, Xiao-Peng Liu, Hai-Hua Lu, Li Rao, Liang-Qiu Lu, Andre M. Beauchemin, Wen-Jing Xiao
Summary: This article describes a palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition reaction, which successfully synthesizes a variety of chiral five-membered heterocycles. The key to the success of this reaction is the remote stereoinduction through hydrogen bond, addressing the challenge of generating chiral quaternary stereocenters using substrates with two different acceptors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Linqing Wang, Feiyun Gao, Xiaoyong Zhang, Tianyu Peng, Yingfan Xu, Rui Wang, Dongxu Yang
Summary: In this study, a simple in situ generated magnesium catalyst was used to achieve the enantioselective [2 + 2] cyclization reaction between DPP-imines and alpha-branched allenoates for the first time. Insightful experiments and mechanistic investigations were conducted to reveal the details of the reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Asif Ali Qureshi, Arpula Sanjeeva Kumar, Sachin Chauhan, K. C. Kumara Swamy
Summary: This method provides a regio- and stereoselective thermal [3+2] cycloaddition protocol for the synthesis of 1,4,5-tri/1,5-disubstituted 1,2,3-triazoles using acetoxy allenoates as 1,2-dipoles. Different carbon positions of acetoxy allenoates lead to different triazole cores with good to high yields.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Physical
Ming Bao, Michael P. Doyle
Summary: The [3+n]-cycloaddition reactions using chiral catalysts and racemic cyclopropanes or achiral catalysts and chiral, non-racemic cyclopropanes have proven to be important transformations for the synthesis of carbocyclic and heterocyclic compounds, showing both mechanistic and structural advantages in ring formation.
Article
Chemistry, Organic
Ewelina Kowalska, Mateusz Dyguda, Angelika Artelska, Anna Albrecht
Summary: In this manuscript, a novel method for the synthesis of cyclopenta-[b]-chromenocarbonitrile derivatives through [3+2] cycloaddition reaction has been described. The reaction is initiated by visible light catalysis using Eosin Y as a photocatalyst, and requires the presence of a small amount of photoredox catalyst, anhydrous solvent, and inert atmosphere.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lihua Xie, Yi Li, Shunxi Dong, Xiaoming Feng, Xiaohua Liu
Summary: The study demonstrates that the chiral amide-guanidine-catalyzed reaction can achieve the synthesis of chiral indolin-3-one derivatives with two contiguous tetrasubstituted stereocenters, yielding moderate to good results with high diastereoselectivities and enantioselectivities. A possible working mode was proposed to explain the chiral control of the process.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Haidong Liu, Lifang Tian, Hui Wang, Zhi-Qiang Li, Chi Zhang, Fei Xue, Chao Feng
Summary: gem-Difluorocyclopropane diester has been used as a donor-acceptor cyclopropane in this study for the first time. It participates smoothly in (3 + 2)-cycloadditions with various aldehydes and ketones, resulting in the synthesis of densely functionalized gem-difluorotetrahydrofuran skeletons.
Article
Chemistry, Organic
Xiaoqiang Lei, Juan Feng, Qinglan Guo, Chengbo Xu, Jiangong Shi
Summary: A concise and practical strategy for the synthesis of functionalized rhodanine derivatives is developed via a potassium-carbonate-mediated [3 + 2] -cycloaddition reaction. The strategy exhibits a wide substrate scope and good functional group tolerance, enabling the synthesis of natural product derivatives containing rhodamine skeletons.
Article
Chemistry, Multidisciplinary
Hisako Hashimoto, Kohei Watanabe, Takashi Yoshimoto, Naoki Hayakawa, Tsukasa Matsuo, Hiromi Tobita
Summary: A neutral silylyne complex of molybdenum was synthesized and compared with its tungsten analog. The molybdenum complex exhibited a dominant monomer form in solution and reacted faster with alkynes compared to the tungsten complex. The formation of silaiminoacyl complexes through [2+3] cycloaddition was achieved and confirmed by various measurements and DFT calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Xinyi Wan, Shan Wang, Chengjun Wu, Jianbo Gan, Cunde Wang
Summary: The synthesis of polysubstituted quinolines was investigated through a Yb(OTf)(3)-mediated annulation of cyclopropane-1,1-dicarbonitriles and 2-aminobenzaldehydes, resulting in generally good yields. The cascade reaction involves ring opening, intermolecular nucleophilic addition, intramolecular nucleophilic addition, and demalononitrile aromatization, with the malononitrile group acting as a removable directing group mediated by Yb(OTf)(3).
