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      Dr. Xiao-Song Xue (薛小松)-Associate Professor: Xiao-Song Xue was born in 1983 in Chongqing. He received his PhD in organic chemistry from Nanking University in 2013 under the supervision of Prof. Jin-Pei Cheng. In the same year, he joined Nanking University as an Assistant Professor and was promoted to Associate Professor in 2016. He was a Visiting Scholar in Prof. Ken. N Houk group at University of California, Los Angeles in 2017-2019. His current research interests include: 1) Reactivity and Selectivity Rules in Organic Reactions; 2) Reaction Dynamics, and 3) The Chemistry of the Halogens. His work has been published in Chem. Rev. J. Am. Chem. Soc., Angew. Chem. Int. Ed., Org. Lett., J. Org. Chem., etc.

    

Publications

    [1] Biying Zhou, Moriana K. Haj, Eric N. Jacobsen, Houk, K. N.,* Xiao-Song Xue,* Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes, J. Am. Chem. Soc. 2018. 140, 15206.

    [2] Jingjing Zhang, Yang Jin-Dong, Hanliang Zheng, Xiao-Song Xue,* Herbert Mayr,* Cheng Jin-Pei. Exploration of the Synthetic Potential of Electrophilic Trifluoromethylthiolating and Difluoromethylthiolating Reagents, Angew. Chem. Int. Ed. 2018, 57, 12690.

    [3] Xiao-Song Xue,# Cooper S. Jamieson,# Marc Garcia-Borràs,# Xiaofei Dong,# Zhongyue Yang, K. N. Hou Ambimodal Trispericyclic Transition State and Dynamic Control of Periselectivity. J. Am. Chem. Soc. 2019. 141, 1217. (# equally contribution)

    [4] Yang Jin-Dong, Ji Pengju, Xiao-Song Xue, Jin-Pei Cheng* Recent Advances and Advisable Applications of Bond Energetics in Organic Chemistry, J. Am. Chem. Soc. 2018. 140, 8611.

    [5] Di Wang, Xiao-Song Xue, Kendall N. Houk,* and Zhuangzhi Shi.* Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes, Angew. Chem. Int. Ed. 2018, 16861.

    [6] Zhengwei Guo, Man Li, Xue-Qing Mou, Gang He,* Xiao-Song Xue*, Gong Chen* Radical C–H Arylation of Oxazoles with Aryl Iodides: dppf as an Electron-Transfer Mediator for Cs2CO3. Org. Lett., 2018, 20, 1684.

    [7] Wang, Zhen, Wang, Fang, Xiao-Song Xue,* Ji, Pengju,* Acidity Scale of N-Heterocyclic Carbene Precursors: Can We Predict the Stability of NHC–CO2 Adducts? Org. Lett., 2018. 20, 6041.

    [8] Xiao-Song Xue, Levandowski, Brian J., Cyndi Qixin He, Houk, K. N.,* Origins of Selectivities in the Stork Diels–Alder Cycloaddition for the Synthesis of (±)-4-Methylenegermine, Org. Lett., 2018. 20, 6108.

    [9] Li, Man, Yueqian Sang, Xiao-Song Xue,* Cheng, Jin-Pei. Origin of Stereocontrol in Photoredox Organocatalysis of Asymmetric α-Functionalizations of Aldehydes. J. Org. Chem. 2018. 83, 3333.

    [10] Wang Zhen, Zheng Yongjun, Zheng Yong, Xiao-Song Xue,* Ji Pengju * A Systematic Theoretical Study on the Acidities for Cations of Ionic Liquids in Dimethyl Sulfoxide J. Phys. Chem. A 2018, 122, 5750.

    [11] Li, Man, Zhen, Hanliang, Xiao-Song Xue,* Cheng, Jin-Pei. Ordering the relative power of electrophilic fluorinating, trifluoromethylating, and trifluoromethylthiolating reagents: A summary of recent efforts. Tetrahedron Lett.2018, 59, 1278. (Invited review)

    [12] Zhu Jiansheng, Zheng Hanliang,Xiao-Song Xue*, Xiao Yisa, Liu Yafei, Shen Qilong,* Carbon-Selective Difluoromethylation of Soft Carbon Nucleophiles with Difluoromethylated Sulfonium Ylide, Chin. J. Chem.2018. 36, 1069.

    [13] Man, Li, Huiying, Kang, Xiao-Song Xue*, Jin-Pei, Cheng, Computational Study of the Trifluoromethyl Radical Donor Abilities of CF3 Sources, Acta Chim. Sinica 2018, 76, 988-996. (Invited contribution)

    [14] Li, Man, Xiao-Song Xue,* Cheng, Jin-Pei. Mechanism and Origins of Stereoinduction in Natural Cinchona Alkaloid Catalyzed Asymmetric Electrophilic Trifluoromethylthiolation of β-Ketoesters with N-Trifluoromethylthiophthalimide as Electrophilic SCF3 Source. ACS Catal., 2017, 7, 7977.

    [15] Li, Man, Zhou, Biying, Xiao-Song Xue,* Cheng, Jin-Pei. Establishing the Trifluoromethylthio Radical Donating Abilities of Electrophilic SCF3-Transfer Reagents. J. Org. Chem. 2017. 82, 8697.

    [16] Xue, Xiao-Song,# Ji, Pengju,# Zhou, Biying, Cheng, Jin-Pei*. The Essential Role of Bond Energetics in C–H Activation/Functionalization. Chem. Rev. 2017, 117, 8622. (# equally contribution)

    [17] Jiang, Shan, Yan, Tai-Shan, Han, Yong-Chao, Cui, Li-Qian, Xiao-Song Xue,* Zhang, Chi* Hypervalent-Iodine-Mediated Formation of Epoxides from Carbon(sp2)–Carbon(sp3) Single Bonds. J. Org. Chem. 2017, 82, 11691.

    [18] Li, Yao, He, Qixin Cyndi, Gao, Fei-Xiang, Li, Zhen, Xiao-Song Xue, Li, Xin,* Houk, K. N.,* Cheng, Jin-Pei. Design and Applications of N-tert-Butyl Sulfinyl Squaramide Catalysts. Org. Lett. 2017, 19, 1926.

    [19] Yang, Jin-Dong, Wang, Ya, Xiao-Song Xue,* Cheng, Jin-Pei*. A Systematic Evaluation of the N-F Bond Strength of Electrophilic N-F Reagents: Hints for Atomic Fluorine Donating Ability. J. Org. Chem. 2017, 82, 4129.

    [20] Li, Man., Wang, Ya, Xiao-Song Xue,* Cheng, Jin-Pei. A Systematic Assessment of Trifluoromethyl Radical Donor Abilities of Electrophilic Trifluoromethylating Reagents. Asian J. Org. Chem. 2017. 6, 235.

    [21] Zhou, Biying, Xiao-Song Xue,* Cheng, Jin-Pei. Theoretical study of Lewis acid activation models for hypervalent fluoroiodane reagent: The generality of “F-coordination” activation model. Tetrahedron Lett. 2017, 58,1287.

    [22] Zhou, Biying, Yan, Taishan, Xiao-Song Xue,* Cheng, Jin-Pei. Mechanism of Silver-Mediated Geminal Difluorination of Styrenes with a Fluoroiodane Reagent: Insights into Lewis-Acid-Activation Model. Org. Lett. 2016, 18, 6128.

    [23] Yan, Taishan., Zhou, Biying, Xiao-Song Xue,* Cheng, Jin-Pei*. Mechanism and Origin of Unexpected Chemoselectivity in Fluorocyclization of o-Styryl benzamides with a Hypervalent Fluoroiodane Reagent. J. Org. Chem. 2016, 81, 9006.

    [24] Li, Man., Guo, Jinping, Xiao-Song Xue, * Cheng, Jin-Pei*. Quantitative Scale for the rifluoromethylthio Cation-Donating Ability of Electrophilic Trifluoromethylthiolating Reagents. Org. Lett. 2016, 18, 264.

    [25] Li, Man, Xiao-Song Xue,* Guo, Jinping, Wang, Ya, Cheng, Jin-Pei*.An Energetic Guide for Estimating Trifluoromethyl Cation Donor Abilities of Electrophilic Trifluoromethylating Reagents: Computations of X–CF3 Bond Heterolytic Dissociation Enthalpies. J. Org. Chem. 2016, 81, 3119.

    [26] Xue, Xiao-Song, * Wang, Ya, Man, Li, Cheng, Jin-Pei*. Comprehensive Energetic Scale for Quantitatively Estimating the Fluorinating Potential of N–F Reagents in Electrophilic Fluorinations. J. Org. Chem. 2016, 81, 4280.

    [27] Zhang, Panpan, Li , Man, Xiao-Song Xue,* Xu, Chunfa, Zhao, Qunchao, Liu, Yafei, Wang, HaoYang, Guo, Yinlong, Lu, Long,* Shen, Qilong.* N-Trifluoromethylthiodibenzenesulfonimide: A Shelf-Stable, Broadly Applicable Electrophilic Trifluoromethylthiolating Reagent. J. Org. Chem.2016, 81, 7486.

    [28] Dong, Nan, Zhang, Zhi. Pei, Xiao-Song Xue, Li, Xin*, Cheng, Jin-Pei. Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para-Quinone Methides. Angew. Chem. Int. Ed.2016, 55, 1460.

    [29] Xue, Xiao-Song, * Wang, Ya, Chen, Yang, Ji, Pengju, Cheng, Jin-Pei*. Toward Prediction of the Chemistry in Ionic Liquids: An Accurate Computation of Absolute pKa Values of Benzoic Acids and Benzenethiols. J. Org. Chem. 2015, 80, 8997.

    [30] Wang, Feng, Yang, Chen, Xiao-Song Xue, Li, Xin., Cheng, Jin-Pei. A Highly Efficient Chirality Switchable Synthesis of Dihydropyran-Fused Benzofurans by Fine-Tuning the Phenolic Proton of β-Isocupreidine (β-ICD) Catalyst with Methyl. Chem. Eur. J. 2015, 21, 10443.

    [31] Xue, Xiao-Song, Chen, Yang, Li, Xin,* Cheng, Jin-Pei*. A Computational Study on the pKa Shifts of Proline Induced by Hydrogen-bond Donating Co-catalysts J. Org. Chem.2014, 79, 1166.

    [32] Chen, Yang,Xiao-Song Xue, Li, Xin,* Cheng, Jin-Pei*. Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide J. Org. Chem. 2014, 79, 4340.

    [33] Xue, Xiao-Song, Chen, Yang, Li, Xin, Cheng, Jin-Pei*. Computation of Standard Equilibrium Acidity of C-H Acids in Ionic Media: Shedding Light on Predicting Changes of Chemical Behavior by Switching Solvent System from Molecular to Ionic. Org. Chem. Front. 2014, 1, 176.

    [34] Xue, Xiao-Song, Li, Xin, Yu, Ao,* Chen, Yang, Song, Chan, Cheng, Jin-Pei*. Mechanism and Selectivity of Bio-inspired Novel Cinchona Alkaloid Derivatives Catalyzed Asymmetric Olefin Isomerization: A Computational Study. J. Am. Chem. Soc. 2013, 135, 7462.

    [35] Yang, Chen, Xiao-Song Xue, Jin, Jialu, Li, Xin*, Cheng, Jin-Pei*. Theoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis. J. Org. Chem. 2013, 78, 7076.

    [36] Li, Xin*, Yang, Chen, Jin, Jialu, Xiao-Song Xue, Cheng, Jin-Pei*. Synthesis of Optically Enriched Spirocyclic Benzofuran-2-ones via Bifunctional Thiourea Catalyzed Double-Michael Addition of Benzofuran-2-ones to Dienones. Chem. Asian J. 2013, 8, 4.

    [37] Li, X,* Liu. Cong, Xiao-Song Xue, Cheng, Jin-Pei*. Enantioselective Organocatalyzed Sulfenylation of 3-Substituted Oxindoles. Org. Lett. 2012, 4374.

    [38] Li, Xin,*Xiao-Song Xue, Liu, Cong, Wang, Bin, Tan, Boxuan, Jin, Jialu, Zhang, Yueyan, Dong, Nan, Cheng, Jin-Pei*. Asymmetric Michael Addition Reactions of 3-Substituted Benzofuran-2(3H)-ones to Nitroolefins Catalyzed by a Bifunctional Tertiary-amine thiourea. Org. Biomol. Chem. 2012, 10, 413.

    [39] Yu, Ao*, Xiao-Song Xue, Wang, Jian., Wang, Huikai., Wang, Yongjian, The Effects of Insertion of Nitrogen Atoms on the Aromatic Nitrogen-Containing Compounds: a Potential Approach for Designing Stable Radical Molecular Materials. J. Phys. Org. Chem. 2012, 25, 92.

    [40] Li, Xin*, Zhang, Yuanyan, Xiao-Song Xue, Jin, Jialu, Tan, Boxuan, Liu, Cong, Dong, Nan, Cheng, Jin-Pei*. Asymmetric Michael Addition Reactions between 3-Substituted Benzofuran-2(3H)-ones and 1,1-Bis(phenylsulfonyl)ethylene Catalyzed by Bifunctional Catalysts Containing Tertiary Amine and Thiourea Groups. Eur. J. Org. Chem. 2012, 1774.

    [41] Xue, Xiao-Song, Yu, Ao,* Cai, Yu, Cheng, Jin-Pei. A Computational Reinvestigation of the Formation of N-Alkylpyrroles via Intermolecular Redox Amination. Org. Lett. 2011, 13, 6054.

    [42] Hou, Yanhui,* Wang, Huikai, Li, Zhi, Liu, Yongshen, Wan, Xianjian,Xiao-Song Xue, Chen, Yongsheng, Yu, Ao. Organic Radicals Based on Phenalenyl and Verdazyl Units. Tetrahedron Lett. 2011, 52, 3670.

    [43] Yu, Ao,* Wang, Jijian, Xiao-Song Xue, Wang, Yongjian*. Theoretical Study of the Peripheral Disulfide Bridge Substituent Effects on the Antioxidant Properties of Naphthyridine Diol Derivatives. J. Phys. Chem. A. 2010, 114, 1008.

    [44] Zhang, Huaqiang, Wan, Xianjian, Xiao-Song Xue, Li, Yanqin, Yu, Ao, Chen, Yongsheng*. Eur. J. Org. Chem. 2010, 1681.

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