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Rhodium-Catalyzed [5 + 1 + 2] Cycloaddition of Yne-3-acyloxy-1,4- enynes (YACEs) and Carbon Monoxide: Reaction Development and Mechanism Qi Cui,† Pan Zhang,† Bing-Wen Li,† Yi Jin, Qianwei Zhang, Hong-Xi Bai, and Zhi-Xiang Yu* ACS Catal. 2024, 14, 14595−14605.
Ni(0)-Catalyzed Rearrangement of Vinylcyclobutanones (VCBOs) to Synthesize Six-Membered Non-Conjugated Enones Jiguo Ma, Jicheng Duan, and Zhixiang Yu* Angew. Chem. Int. Ed. 2024, e202417407
How to Suppress C(sp2)–Rh–C(sp3) Reductive Elimination and Insert CO to Achieve Rhodium-Catalyzed [5 + 2 + 1] Cycloaddition of Yne-vinylcyclopropanes and CO: Answers from Experimental and Computational Investigation Zhiqiang Huang, Yi Jin, Sixuan Zhao, Pan Zhang, Wei Liao, and Zhi-Xiang Yu*ACS Catal. 2024, 14, 12734−12742
A Desymmetric Dearomatization Cyclopropanation of [2.2]Paracyclophane Dong Chen†, Yi Zhou†, Chen-Ho Tung, Zhi-Xiang Yu and Zhenghu Xu CCS Chemistry. , 2024; 0:1–13.
C–H functionalization of 2-alkyl tryptamines: direct assembly of azepino[4,5-b]indoles and total synthesis of ngouniensines Kejing Xie,‡ Zeyuan Shen,‡ Peng Cheng, Haoxiang Dong, Zhi-Xiang Yu * and Liansuo Zu *Chem. Sci. , 2024, Advance Article, 10.1039/d4sc02802c
O-to-O acyl transfer for epimerization-free peptide C-terminal salicylaldehyde ester synthesis Wang Xia, Bing-Wen Li, Zhixiang Zhong, Jiamei Liu, Han Liu, Zhi-Xiang Yu & Xuechen Li Nat. Synth. 2024, https://doi.org/10.1038/s44160-024-00570-0
Pd(II)/N,N′‑Disulfonyl Bisimidazoline-Catalyzed Enantioselective Synthesis of Cyclic Quaternary Centers and Mechanistic Investigations Yu-Xin Wang,§ Chen-Long Li,§ Yin-Ping Liu, Wen-Juan Hao, Zhi-Xiang Yu,* and Bo Jiang*J. Org. Chem. 2024, XXX, XXX-XXX
Catalytic (4+2) Annulation via Regio- and Enantioselective Interception of in-situ Generated Alkylgold Intermediate Ming Bao+, Yi Zhou+, Haoxuan Yuan+, Guizhi Dong, Chao Li, Xiongda Xie, Kewei Chen, Kemiao Hong,Zhi-Xiang Yu,* and Xinfang Xu*Angew. Chem. Int. Ed. 2024, e202401557.
Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide Chen-Long Li, Zhi-Xiang Yu*Chinese Journal of Organic Chemistry, 2024, 44, 1045-1068.
Desulfurdioxidative N-N Coupling of N-Arylhydroxylamines and N-Sulfinylanilines: Reaction Development and Mechanism Linwei Li#, Yi Zhou#, Zhenguo Xi, Zhaoquan Guo, Ji-Cheng Duan, Zhi-Xiang Yu*, and Hongyin Gao*Angew. Chem. Int. Ed. 2024, e202406478.
Selective Hydrofunctionalization of Alkenyl Fluorides Enabled by Nickel-Catalyzed Hydrogen Atoms and Group Transfer: Reaction Development and Mechanistic Study Fan Chen,§ Qianwei Zhang,§ Yingying Li, Zhi-Xiang Yu,* and Lingling Chu*J. Am. Chem. Soc. 2024. 146, 11418−11431.
Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature Han-Xiao Li and Zhi-Xiang Yu*Org. Lett. 2024. 26, 3458−3462.
Rhodium-Catalyzed [5 + 1 + 2] Cycloaddition of Yne-3-Acyloxy-1,4-Enynes (YACEs) and Carbon Monoxide: Reaction Development and Mechanism Qi Cui,† Pan Zhang,† Bing-Wen Li,† Yi Jin, Qianwei Zhang, Hong-Xi Bai, and Zhi-Xiang Yu*ChemRxiv 2024. 10.26434/chemrxiv-2024-rhl1f
Dynamically or Kinetically Controlled? Computational Study of the Mechanisms of Electrophilic Aminoalkenylation of Heteroaromatics with Keteniminium Ions Pan Zhang and Zhi-Xiang Yu J. Org. Chem. 2024, 89, 4326−4335.
Rh(I)-Catalyzed [4+3]/[4+1] Cycloaddition of Diene-Vinylcyclopropanes and Carbon Monoxide to Access Angular 5/7/5 Tricycles Jun Yang, Pan Zhang, Zeyuan Shen, and Zhi-Xiang Yu*Chem. Eur. J. 2023, e202303407.
Rhodium-Catalyzed [7 + 1] Cycloaddition of Exocyclic 1,3- Dienylcyclopropanes and Carbon Monoxide Zhiqiang Huang,† Xin Wang,† Yi Jin, Zuwei Wang, and Zhi-Xiang Yu*Org. Lett. 2023, 25, 8829-8833.
1,5-X Insertions of Free Alkylidene Carbenes: A Theoretical Study Yi Zhou, Prof. Dr. Zhi-Xiang Yu*Asian J. Org. Chem. 2023, e202300440.
Catalytic 4-exo-dig carbocyclization for the construction of furan-fused cyclobutanones and synthetic applications Kemiao Hong#, Yi Zhou#, Haoxuan Yuan, Zhijing Zhang, Jingjing Huang, Shanliang Dong, Wenhao Hu, Zhi-Xiang Yu* & Xinfang Xu*Nat. Commun. 2023, 14, 6378.
Rh-Catalyzed [4+1] Reaction of Cyclopropyl-Capped Dienes (but not Common Dienes) and Carbon Monoxide: Reaction Development and Mechanistic Study Yusheng Yang#, Han-Xiao Li#, Tian-Yu Zhu, Zi-You Zhang and Zhi-Xiang Yu*J. Am. Chem. Soc. 2023, 145, 17087−17095.
Direct insertion into the C–C bond of unactivated ketones with NaH-mediated aryne chemistry Fan Luo#, Chen-Long Li#, Peng Ji, Yuxin Zhou, Jingjing Gui, Lingyun Chen, Yuejia Yin, Xinyu Zhang, Yanwei Hu, Xiaobei Chen, Xuejun Liu, Xiaodong Chen, Zhi-Xiang Yu*, Wei Wang*, Shi-Lei Zhang* Chem, 2023, 10.1016/j.chempr.2023.05.032.
Regioselective umpolung para-C–H functionalization of arylhydroxylamines Zhenguo Xi, Xi-Jia Liu, Zhaoquan Guo, Zhiwei Gao, Zhi-Xiang Yu & Hongyin Gao Nature Synthesis, 2023, 10.1038/s44160-023-00293-8.
Kinetic, Thermodynamic, and Dynamic Control in Normal vs. Cross [2 + 2] Cycloadditions of Ene-Keteniminium Ions: Computational Understanding, Prediction, and Experimental Verification Pan Zhang and Zhi-Xiang Yu*J. Am. Chem. Soc. 2023, 145, 9634–9645.
Computational Study of Mechanisms and Tether Length Effects of Rh-Catalyzed [3+2] and [3+2+1] Reactions of Ene/Yne- Vinylcyclopropanes Guan-Yu Zhang, Mu Lin, and Zhi-Xiang Yu*Chem Asian J. 2023, e202300032
Antrodiellin B/hypnophilin/coriolin and strained 5/5/5 and 5/6/4 skeletons via [5+2+1]/epoxidation/transannular radical cyclization Lu-Ning Wang, Zhiqiang Huang, Zhi-Xiang Yu*Cell Reports Physical Science 2023, 4, 101302.
Synthesis of Polycyclic n/5/8 and n/5/5/5 Skeletons Using Rhodium-Catalyzed [5 + 2 + 1] Cycloaddition of Exocyclic-ene-vinylcyclopropanes and Carbon Monoxide Lu-Ning Wang#, Zhiqiang Huang#, and Zhi-Xiang Yu*Org. Lett. 2023, 25, 1732–1736.
Strain-Release-Controlled [4 + 2 + 1] Reaction of Cyclopropyl-Capped Diene-ynes/Diene-enes and Carbon Monoxide Catalyzed by Rhodium Chen-Long Li#, Yusheng Yang#, Yi Zhou#, Zhao-Chen Duan, and Zhi-Xiang Yu*J. Am. Chem. Soc., 2023, 145, 5496–5505.
Unprecedented endo-oxidative cyclometallation and [4 + 3] cycloaddition of diene-vinylcyclopropanes Jun Yang#, Pan Zhang#, Zeyuan Shen, Yi Zhou, Zhi-Xiang Yu*Chem. 2023, 9, 10.1016/j.chempr.2023.01.020.
Metalla-Claisen Rearrangement in Gold-Catalyzed [4+2] Reaction: A New Elementary Reaction Suggested for Future Reaction Design Jing Liu+, Yusheng Yang+, Weiming Shi+, and Zhi-Xiang Yu*Angew. Chem. Int. Ed. 2023, e202217654.
Formal Hydrotrimethylsilylation of Styrenes with Anti-Markovnikov Selectivity Using Hexamethyldisilane Xin Wang, Zhi-Xiang Yu*, and Wen-Bo Liu*Org. Lett. 2022, 24, 8735–8740
DFT Study of Mechanism and Stereochemistry of Nickel-Catalyzed trans-Arylative Desymmetrizing Cyclization of Alkyne-Tethered Malononitriles Yu-Qing Zheng, Chen-Long Li, Wen-Bo Liu*, and Zhi-Xiang Yu*J. Org. Chem. 2022, 87, 16079–16083
Dual Activation Strategy to Achieve C–C Cleavage of Cyclobutanes: Development and Mechanism of Rh and Zn Cocatalyzed [4 + 2] Cycloaddition of Yne-Vinylcyclobutanones Guan-Yu Zhang†, Pan Zhang†, Bing-Wen Li†, Kang Liu, Jun Li, and Zhi-Xiang Yu*J. Am. Chem. Soc. 2022, 144, 21457–21469
Atroposelective Synthesis of N-Arylindoles via Enantioselective N–H Bond Insertion Chao Niu#, Yi Zhou#, Qiang Chen, Yan Zhu, Shengbiao Tang, Zhi-Xiang Yu*, and Jiangtao Sun*Org. Lett. 2022, 24, 7428–7433
Syntheses of (+)-Antrodiellin B, (−)-Hypnophilin and (−)-Coriolin and Strained 5/5/5 and 5/6/4 Skeletons via [5+2+1]/Epoxidation/Transannular Radical Cyclization Lu-Ning Wang, Zhiqiang Huang and Zhi-Xiang Yu*ChemRxiv 2022. 10.26434/chemrxiv-2022-lxlfz.
Selective Enyne Ring-Closing Metathesis with Main Group Metal Catalysts Yi Wang, Lian-Gang Zhuo, Chi Zhang, and Zhi-Xiang Yu*ChemRxiv 2022. 10.26434/chemrxiv-2022-7bm1b
Strain-Release Controlled [4+2+1] Reaction of Cyclopropyl-Capped Diene-Ynes/Diene-enes and CO Catalyzed by RhodiumChen-long Li, Yusheng Yang, Zhao-Chen Duan, Yi Zhou, Zhi-Xiang, Yu*ChemRxiv 2022, 10.26434/chemrxiv-2022-9g62z-v2
Total Synthesis of Clovan-2,9-dione via [3 + 2 + 1] Cycloaddition and Hydroformylation/Aldol Reaction Yi Zhou, Jun-Long Qin, Wenbo Xu, and Zhi-Xiang Yu* Org. Lett. 2022, 24, 5902–5906.
Why [4 + 2 + 1] but Not [2 + 2 + 1]? Why Allenes? A Mechanistic Study of the Rhodium-Catalyzed [4 + 2 + 1] Cycloaddition of In Situ Generated Ene–Ene–Allenes and Carbon Monoxide Yusheng Yang, Zi-You Tian, Chen-Long Li, and Zhi-Xiang Yu*. J. Org. Chem. 2022, 87, 10576–10591.
Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades Tian Ye, Feng-Lian Zhang, Hui-Min Xia, Xi Zhou, Zhi-Xiang Yu*, Yi-Feng Wang* Nat. Commun. 2022, 13, 426.
Catalytic Enantioselective Construction of 6-4 Ring-Junction All-Carbon Stereocenters and Mechanistic Insights Jia-Yin Wang, Chen-Long Li, Ting Xu, Meng-Fan Li, Wen-Juan Hao, Shu-Jiang Tu, Jianyi Wang,* Guigen Li, Zhi-Xiang Yu,* and Bo Jiang* Chin. J. Chem. 2022, 40, 1767.
Six-Step Total Synthesis of Isohirsut-4-ene through [5+2+1] Cycloaddition and Transannular Epoxide–Alkene Cyclization Jing Liu§, Yi Zhou§, and Zhi-Xiang Yu*. Org. Lett. 2022, 24, 1444-1447.
Mechanism and Stereochemistry of Rhodium-Catalyzed [5 + 2 + 1] Cycloaddition of Ene−Vinylcyclopropanes and Carbon Monoxide Revealed by Visual Kinetic Analysis and Quantum Chemical Calculations Yi Wang, Wei Liao, Yuanyuan Wang, Lei Jiao, and Zhi-Xiang Yu* J. Am. Chem. Soc. 2022, 144, 2624.
Palladium-Catalyzed [3 + 2] Annulation of Alkynes with Concomitant Aromatic Ring Expansion: A Concise Approach to (Pseudo)azulenes
Fulin Zhou, Weiming Shi, Xingrong Liao, Yudong Yang*, Zhi-Xiang Yu*, and Jingsong You* ACS Catal. 2022, 12,676–686.
Ynamide Protonation-Initiated Cis-Selective Polyene Cyclization and Reaction Mechanism J.asheng Yao†, Chen-Long Li†, Xing Fan, Zhou Wang, Zhi-Xiang Yu* and Junfeng Zhao* CCS Chem. 2022, 4, 2991–3001.
A Formal [3+3+1] Reaction of Enyne-Methylenecyclopropanes through Au(I)-Catalyzed Enyne Cycloisomerization and Rh(I)-Catalyzed [6+1] Reaction of Vinylspiropentanes and CO
Dr. Chen-Long Li, Yusheng Yang, Yi Zhou, Prof. Dr. Zhi-Xiang Yu* Asian J. Org. Chem. 2022, 11, e202100571.
Synthesizing Molecules with Linear Tricyclic 5/5/5 and 6/5/5 Skeletons via [5 + 2 + 1]/Ene Strategy J.ng Liu, Yi Zhou, Jiaqi Zhu, and Zhi-Xiang Yu*. Org. Lett. 2021, 23, 7566-7570.
(Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl–Ene Reaction Pathan Mosim Amin, Qi Cui, Shaozhong Wang*, Zhi-Xiang Yu*. Org. Lett. 2021, 23, 5669–5673.
Ni-catalyzed hydroaminoalkylation of alkynes with amines Wei-Wei Yao, Ran Li, Hao Chen, Ming-Kai Chen, Yu-Xin Luan, Yi Wang , Zhi-Xiang Yu* and Mengchun Ye*Nat. Commun. 2021, 12, 3800.
Co-Catalyzed Asymmetric Intramolecular [3+2] Cycloaddition of Yne-Alkylidenecyclopropanes and its Reaction Mechanism Xiong Xiao and Zhi-Xiang Yu*. Chem. Eur. J. 2021, 27, 7176–7182.
Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5‑Imino-2-Tetrahydrofuranyl Methanamine Derivatives Xiao-Jun Deng, Hui-Xia Liu, Lu-Wen Zhang, Guan-Yu Zhang, Zhi-Xiang Yu,* and Wei He* J. Org. Chem. 2021, 86, 235−253.
Rhodium(I)-Catalyzed Three-Component [4+2+1] Cycloaddition of Two Vinylallenes and CO Qi Cui, Zi-You Tian, and Zhi-Xiang Yu* Chem. Eur. J. 2021, 27, 5638 – 5641
Density Functional Theory Study of Mechanisms of [8 + 2] Cycloadditions of Dienylfurans/Dienylisobenzofurans with DMAD Qi Cui, Yuanyuan Chen, James W. Herndon, and Zhi-Xiang Yu* J. Org. Chem. 2021, 86, 1419−1429.
A Combined Computational and Experimental Study of Rh- Catalyzed C−H Silylation with Silacyclobutanes: Insights Leading to a More Efficient Catalyst System Linxing Zhang,# Kun An,# Yi Wang,# Yun-Dong Wu, Xinhao Zhang,* Zhi-Xiang Yu,* and Wei He* J. Am. Chem. Soc. 2021, 143, 3571.
Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Eight-Membered Carbocycles: an Update from 2010 to 2020 Wang Lu-Ning, Yu Zhi-Xiang*Chinese Journal of Organic Chemistry, 2020, 40, 3536-3558.
Mechanism and Regioselectivity of Intramolecular [2+2] Cycloaddition of Ene–Ketenes: A DFT Study Xing Fan,Pan Zhang, Yi Wang, and Zhi-Xiang Yu* Eur. J. Org. Chem. 2020, 37, 5985.
Synergy of activating substrate and introducing C–H···O interaction to achieve Rh2(II)-catalyzed asymmetric cycloisomerization of 1,n-enynes Rui Wu, Kai Chen, Jun Ma, Zhi-Xiang Yu*, and Shifa Zhu*Science China Chemistry 2020, 63, 1230–1239.
Transient-axial-chirality controlled asymmetric rhodium-carbene C(sp2)-H functionalization for the synthesis of chiral fluorenes Kuiyong Dong, Xing Fan, Chao Pei, Yang Zheng, Sailan Chang, Ju Cai, Lihua Qiu, Zhi-Xiang Yu* and Xin-fang Xu*Nature Communications2020, 11, 2363
Remote γ-C(sp3)–H Alkylation of Aliphatic Carboxamides via an Unexpected Regiodetermining Pd Migration Process: Reaction Development and Mechanistic Study Ya Li, Pan Zhang, Yue-Jin Liu, Zhi-Xiang Yu*, and Bing-Feng Shi* ACS Catal. 2020, 10, 8212–8222
Lewis Base-Catalyzed Amino-Acylation of Arylallenes via C–N Bond Cleavage: Reaction Development and Mechanistic Studies Zheng-Bing Zhang, Yusheng Yang, Zhi-Xiang Yu*, and Ji-Bao Xia* ACS Catal. 2020, 10, 5419–5429
Mechanistic Study on Gold-Catalyzed Cycloisomerization of Dienediynes Involving Aliphatic C−H Functionalization and Inspiration for Developing a New Strategy to Access Polycarbocycles Yi Wang, Pei-Jun Cai, and Zhi-Xiang Yu* J. Am. Chem. Soc. 2020, 142, 2777−2786
Symmetric C···H···C Hydrogen Bonds Predicted by Quantum Chemical Calculations Yi Wang and Zhi-Xiang Yu* J. Org. Chem. 2020, 85, 397−402
NHC-Boryl Radical Catalysis for Cycloisomerization With C–C Triple Bond Reorganization Ai-Qing Xu, Feng-Lian Zhang, Tian Ye, Zhi-Xiang Yu*, and Yi-Feng Wang* CCS Chem. 2019, 1, 504–512
Rh-Catalyzed Cycloisomerization of 1,7-Ene-Dienes to Synthesize trans-Divinylpiperidines: A Formal Intramolecular Addition Reaction of Allylic C-H Bond into Dienes Qi Cui, Wei Liao, Zi-You Tian, Qian Li, and Zhi-Xiang Yu Org. Lett. 2019, 21, 7692-7696
A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond Wenzhi Ji, Chen-Long Li, Hui Chen, Zhi-Xiang Yu* and Xuebin Liao* Chem. Commun. 2019, 55, 12012
Synthesis of Quaternary Carbon-Centered Benzoindolizidinones via Novel Photoredox-Catalyzed Alkene Aminoarylation: Facile Access to Tylophorine and Analogues Chao Zhang, Yi Wang, Yugang Song, Hongying Gao, Yonghui Sun, Xiuyun Sun, Yiqing Yang, Ming He, Zimo Yang, Lingpeng Zhan, Zhi-Xiang Yu*, and Yu Rao*CCS Chem. 2019, 1, 352−364
Divergent Synthesis of Oxa-Cyclic Nitrones through Gold(I)- Catalyzed 1,3-Azaprotio Transfer of Propargylic a-Ketocarboxylate Oximes: Experimental and DFT Studies Chunhong Wang, Qi Cui, Zhixin Zhang, Zhu-Jun Yao, Shaozhong Wang*, and Zhi-Xiang Yu* Chem. Eur. J. 2019, 25, 9821 – 9826
Asymmetric Synthesis of Azepine-Fused Cyclobutanes from Yne- Methylenecyclopropanes Involving Cyclopropanation/C−C Cleavage/Wagner−Meerwein Rearrangement and Reaction Mechanism Chen-Long Li and Zhi-Xiang Yu* J. Org. Chem. 2019, 84, 9913−9928
Type-II Pauson-Khand reaction of 1,8-enyne in the attempt of building 7/5 ring of (-)-caribenol A and DFT understanding Yang Wang, Kang Liu, Zhi-Xiang Yu*, Yanxing Jia*Tetrahedron Lett. 2019, 60, 151001
Understanding Regioselectivities of Corey–Chaykovsky Reactions of Dimethylsulfoxonium Methylide (DMSOM) and Dimethylsulfonium Methylide (DMSM) toward Enones: A DFT Study. Yu Xiang, Xing Fan, Pei-Jun Cai, Zhi-Xiang Yu* Eur. J. Org. Chem. 2019, 582-590
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