Article
Chemistry, Applied
Takeshi Yasui, Yuya Nakazato, Koutarou Kurisaki, Yoshihiko Yamamoto
Summary: In this study, a Rh-catalyzed asymmetric [2+2+2] cycloaddition reaction was reported, resulting in the synthesis of enantio-enriched tricyclic cyclohexadienes with a quaternary bridgehead carbon. It was found that the Rh-Phanephos complex was the most suitable catalyst, while Rh-biaryl bisphosphine catalysts were not applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Wei-Hang Miao, Wen-Xia Gao, Xiao-Bo Huang, Miao-Chang Liu, Yun-Bing Zhou, Hua-Yue Wu
Summary: The method described involves a ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, catalyzed by CuX2 or I-2, providing an efficient synthesis route for 3-haloacrylates. This protocol is highly atom economical, exhibits excellent substrate scope, and can be scaled up for gram-scale reactions.
Article
Chemistry, Organic
Luyao Wang, Mengting Li, Zhitao Ning, Xi Zhang, Ying Fu, Zhengyin Du
Summary: An efficient visible-light-assisted, copper-catalyzed tandem radical cyclization of N-propargylindoles with cyclic ethers has been established. A series of 2-oxoalkyl-9H-pyrrolo[1,2-a]indol-9-ones with potential biological activities were synthesized in moderate yields using a dual catalytic system with copper acetate as a transition metal catalyst and eosin Y as a visible light catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Sidi Cheng, Yu Luo, Ting Yu, Jing Li, Chunfang Gan, Shuang Luo, Qiang Zhu
Summary: An unactivated alkene was successfully subjected to 1,2-difunctionalization through a palladium-catalyzed four-component cascade reaction, leading to the convenient synthesis of acetamides with various substituents and pyrrolo-fused heterocycles.
Review
Chemistry, Physical
Yong You, Qun Li, Yan-Ping Zhang, Jian-Qiang Zhao, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: Palladium-catalyzed decarboxylative cycloadditions have emerged as highly efficient methods for constructing structurally diverse carbo- and heterocycles due to their ability to form multiple carbon-carbon or carbon-heteroatom bonds in a single step. This review discusses the achievements and synthetic applications of these reactions involving cyclic carbonates, carbamates, and lactones for accessing oxacyclo-, azacyclo-, and carbocyclic compounds. Mechanistic insights and the challenges and opportunities in this field are also addressed.
Article
Chemistry, Physical
Takeshi Yasui, Keiji Yamada, Rine Tatsumi, Yoshihiko Yamamoto
Summary: In this study, a method for generating vinylallenes through cobalt/photoredox dual-catalysis was reported, allowing the formal 1,8-acyloxy migration of 1,6-diynyl esters. A cascade reaction involving 1,8-acyloxy migration/6 pi-electrocyclization was demonstrated using (hetero)aryl-substituted 1,6-diynyl esters, leading to the formation of arenol derivatives, and the method was also applied to cascade cyclizations involving [2 + 2] or [4 + 2] cycloadditions to furnish various polycyclic molecules.
Article
Chemistry, Organic
Michio Yamada, Yuta Uokawa, Shino Sasaki, Naohiro Iha, Yoshihisa Hashimoto, Yuya Nagasaki, Yutaka Maeda, Mitsuaki Suzuki
Summary: In this study, a one-step strategy for synthesizing cyclobutene-annulated fullerene derivatives (cyclobutenofullerenes) was developed and their electronic properties were characterized. Despite steric strain, cyclobutenofullerenes can be easily prepared through a one-step reaction of C-60 with a secondary propargylic phosphate. Structural analysis of reaction intermediates suggests that the cascade reaction proceeds through a formal [2 + 2] cycloaddition of C-60 with an allene, caused by the 1,3-migration of the propargylic phosphate, followed by an additional 1,3-migration and subsequent 1,2-elimination of the phosphodiester moiety.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ali Nikbakht, Ahmadreza Ebrahimi Valdani, Hossein Zahedian Tejeneki, Alireza Abbasi Kejani, Nahid S. Alavijeh, Felix Bauer, Fatemeh Darvish, Bernhard Breit, Saeed Balalaie
Summary: A diastereoselective cascade annulation between allenoates and in-situ generated isoquinoline N-oxides is reported, leading to the formation of sp3-rich bridged polycyclic heterocycles through an unprecedented non-rearomatized rearrangement. The reaction exhibits high diastereoselectivity and good functional group tolerance, achieving yields of 38-93%. Density functional theory calculations offer insights into the reaction pathway and stereoselectivity.
Article
Chemistry, Organic
Michio Yamada, Yuta Uokawa, Shino Sasaki, Naohiro Iha, Yoshihisa Hashimoto, Yuya Nagasaki, Yutaka Maeda, Mitsuaki Suzuki
Summary: The physicochemical properties of fullerene-based materials can be influenced by the type and mode of addition of functional groups. Developing fullerene derivatives with novel structures is crucial for the advancement of materials science. This study presents an efficient one-step strategy for synthesizing cyclobutene-annulated fullerene derivatives and characterizing their electronic properties.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ivan Rodriguez-Oliva, Noelia Losada-Garcia, A. Sofia Santos, M. Manuel B. Marques, Jose M. Palomo
Summary: Highly stable nanocatalysts were synthesized in aqueous medium at room temperature by in situ formation of Pd nanoparticles embedded in an enzyme net. The synthesized CALB/PdNPs hybrids showed crystalline Pd(0) as the unique metallic species, with spherical nanoparticles ranging in diameter size from 2 to 11 nm. These hybrids were employed as catalyst in C-N/Heck reaction cross-coupling cascade to synthesize substituted azaindoles with high selectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Lele Wang, Ziying Zhang, Huabin Han, Xiongli Liu, Zhanwei Bu, Qilin Wang
Summary: Bridged rings are commonly found in natural products and biologically active molecules, with significant applications in medicinal chemistry, natural product chemistry, synthetic chemistry, material chemistry, and life science. In recent years, new methods for the efficient synthesis of bridged compounds have been developed through the efforts of numerous chemists, providing useful reference for researchers in organic synthesis and related fields.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kai-Wen Hu, Xiao You, Jin-Zheng Wang, Xiaoan Wen, Hongbin Sun, Qing-Long Xu, Zengwei Lai
Summary: The study reports the development of enantioselective desymmetrization of para-quinamines with isocyanates catalyzed by chiral phosphoric acid. The method provides access to functionalized imidazolidin-2-one derivatives with high yields and enantioselectivities under mild reaction conditions. This protocol demonstrates the synthetic utility by enabling easy transformation of chiral imidazolidin-2-one derivatives into valuable scaffolds without disturbing enantiopurity.
Article
Chemistry, Applied
Tianlong Zeng, Jingyang Kong, Hongkai Wang, Lingyan Liu, Weixing Chang, Jing Li
Summary: Substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2 were reported, yielding either spiroketals or oxa-bridged fused heterocycles depending on the substituent on the chalcone. Control experiments elucidated the high chemoselectivity, providing a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jeremy T. Maddigan-Wyatt, Jing Cao, Jhi Ametovski, Joel F. Hooper, David W. Lupton
Summary: Here, an enantioselective catalytic annulation of electron-poor allenes with aminocrotonates is reported. The reaction proceeds via umpolung gamma-amination and beta-umpolung intramolecular conjugate addition. The reaction provides ready access to chiral compounds with high yields and high enantiomeric ratios, and an assisted tandem-catalytic variant is also proposed.
Article
Chemistry, Organic
Hongfang Li, Ijaz Khan, Qun Li, Yong Jian Zhang
Summary: The first Pd-catalyzed asymmetric three-component reaction of 2,3-allenol, aryl iodides, and 2-arylmethylenemolononitriles has been developed, allowing rapid access to substituted tetrahydrofurans with diverse functional groups in good yields and high selectivities. The concise total synthesis of a lignan, (-)-2-episesaminone, has been achieved using a functionalized tetrahydrofuran obtained from this reaction.
Article
Chemistry, Multidisciplinary
Jiarong Shi, Hai Xu, Dachuan Qu, Jia He, Yang Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Hai Xu, Jia He, Jiarong Shi, Liang Tan, Dachuan Qiu, Xiaohua Luo, Yang Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Chunjie Lv, Caiwen Wan, Song Liu, Yu Lan, Yang Li
Article
Chemistry, Multidisciplinary
Dachuan Qiu, Jiarong Shi, Qianyu Guo, Qiuxia Xu, Baosheng Li, Yang Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Multidisciplinary
Jia He, Zizi Jia, Hongcheng Tan, Xiaohua Luo, Dachuan Qiu, Jiarong Shi, Hai Xu, Yang Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Review
Chemistry, Multidisciplinary
Jia He, Dachuan Qiu, Yang Li
ACCOUNTS OF CHEMICAL RESEARCH
(2020)
Review
Chemistry, Multidisciplinary
Jiarong Shi, Lianggui Li, Yang Li
Summary: Arynes are highly active organic intermediates used in the rapid synthesis of substituted arenes, with o-silylaryl triflates being the most frequently employed precursors. The resurgence in aryne chemistry over the past 20 years is largely attributed to the widespread use of Kobayashi's method, which involves fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group. This review provides an overview of the history, achievements, and applications of Kobayashi's method in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.
Article
Chemistry, Multidisciplinary
Jiarong Shi, Lianggui Li, Chunhui Shan, Junli Wang, Zhonghong Chen, Rongrong Gu, Jia He, Min Tan, Yu Lan, Yang Li
Summary: An unprecedented aryne 1,2,3,5-tetrasubstitution was achieved through a reaction involving 3-silylbenzyne and aryl allyl sulfoxide. The mechanism includes regioselective aryne insertion into the S=O bond, [3,6]-sigmatropic rearrangement, and thermal aromatic 1,3-silyl migration cascade.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jiarong Shi, Lianggui Li, Chunhui Shan, Zhonghong Chen, Liang Dai, Min Tan, Yu Lan, Yang Li
Summary: Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne were successfully achieved from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations involve benzyne insertion into the S = O bond and a rare regiospecific anionic [4,5]-sigmatropic rearrangement, leading to the formation of C-O, C-S, and C-C bonds on the C1-, C2-, and C4-position of a benzene ring, respectively. This study introduces new cascade benzyne reaction modes that include distal C-H bond functionalization and dearomatization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Jinlong Zhao, Jiarong Shi, Yang Li
Summary: The benzyne-mediated esterification reaction allows for efficient synthesis of esters from carboxylic acids and alcohols under mild conditions. This reaction can be used for modification of pharmaceutical molecules and synthesis of fatty compounds, with potential applications in various fields.
Article
Chemistry, Multidisciplinary
Lianggui Li, Chunhui Shan, Jiarong Shi, Wensheng Li, Yu Lan, Yang Li
Summary: The stannum-ene reactions of benzyne and cyclohexyne were successfully achieved, with cyclohexyne demonstrating a wide substrate scope and excellent chemoselectivity. DFT calculations revealed that the transition states of the stannum- and hydrogen-ene reactions with cyclohexyne occurred later due to higher distortion energies, resulting in enhanced Pauli repulsion and increased energy gap between the two types of ene reactions, leading to excellent chemoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhonghong Chen, Min Tan, Chunhui Shan, Xiaoling Yuan, Liyuan Chen, Jiarong Shi, Yu Lan, Yang Li
Summary: In this study, both aryne 1,4-disubstitution and 1,2,4-trifunctionalization were achieved by using tertiary amines with a penta-2,4-dien-1-yl moiety. The reactions resulted in the incorporation of a C-N and a C-C bond para to each other on an aryne intermediate through sequential nucleophilic addition and [5,5]-sigmatropic rearrangement. When arynes with 3-tethered electrophiles were used, a cascade regioselective nucleophilic addition, intramolecular cyclization, and remote diastereoselective [5,5]-sigmatropic rearrangement process were observed. Density functional theory (DFT) calculations revealed that the remote diastereoselective control in this reaction system is due to hydrogen-bonding interactions between two C-H hydrogens on the penta-2,4-dien-1-yl chain and the oxygen anion generated upon N-nucleophilic annulation reaction in the [5,5]-sigmatropic rearrangement step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Caiwen Wan, Yueyin Guo, Xiaocui Chen, Rongrong Gu, Jiarong Shi, Yang Li
Summary: In this study, a novel reaction strategy was developed to achieve the formation of multiple C-C bonds on a benzene ring through tandem reactions. The method exhibited high chemical selectivity and functional diversity, and could be applied for the synthesis of 1,2,3,5-tetrasubstituted benzenes.
Article
Chemistry, Organic
Yongjin Guo, Hongpeng Bao, Liyuan Chen, Jiarong Shi, Yang Li
Summary: An insertion reaction of benzyne into the Se=O bond has been successfully achieved, leading to the synthesis of two different types of selenium-containing compounds from various substrates.
Review
Chemistry, Multidisciplinary
Jiarong Shi, Yuanyuan Li, Yang Li
CHEMICAL SOCIETY REVIEWS
(2017)
