Name Xue Xiaosong Gender Male Academic Background Doctor degree Graduate School Nankai University Professional Title associate professor Administrative Post Department/Institute Department of Chemistry Special Talent Address Nankai University, Weijin Road 94# Telephone 13512901971 Email xuexs@nankai.edu.cn Research Group Website http://chem.nankai.edu.cn/dt.aspx?n=A001304358 Research Interest The award of the 1998 and 2013 Nobel prize for computational chemistry is indicative of the key role that calculation has come to play in contemporary science. The overarching goal of our research program is to solve fundamental and challenging problems in organic chemistry using modern computational tools. (1) Understanding the “key” chemical bond in important functional molecules, materials, and bio-systems. (2) Understanding the mechanisms of important and classical reactions (3) Developing new methodology for predicting and understanding amazing chemistry in novel media―ionic liquids. History Xiao-Song Xue was born in 1983 in Chongqing, China. 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. He was a visiting student in Prof. Zhi-Xiang Yu group at Peking University in 2010 and in Prof. Vernon D Parker group at Utah State University in 2012. His current research interests include: 1) understanding the nature and strength of the “key” chemical bonds in important functional molecules, materials, and bio-systems, 2) understanding the mechanisms of important and classical reactions, and 3) developing new methodology for predicting and understanding amazing new chemistry in ionic liquids. Honors and Awards Scientific Achievements & Selected Publications Publications： [1] Mechanism and Origins of Enantioselectivities in Spirobiindane-based Hypervalent Iodine(III) Induced Asymmetric Dearomatizing Spirolactonizations, Hanliang Zheng, Yueqian Sang, K. N. Houk*, Xiao-Song Xue*, Jin-Pei Cheng, J. Am. Chem. Soc. 2019. https://doi.org/10.1021/jacs.9b08243. [2] Controllable Catalytic Difluorocarbene Transfer Enables Access to Diversified Fluoroalkylated Arenes, Xia-Ping Fu,# Xiao-Song Xue,# Xue-Ying Zhang, Yu-Lan Xiao, Shu Zhang, Yin-Long Guo, Xuebing Leng, K. N. Houk*, Xingang Zhang*, Nat. Chem. 2019. DOI 10.1038/s41557-019-0331-9. (# equally contribution) [3] Metal-free directed C-H bond activation and borylation, Jiahang Lv, Xiangyang Chen , Xiao-Song Xue , Binlin Zhao , Yue Zhao , Yi Lu , Jing Zhao , Wei-Yin Sun , Yong Liang, K. N. Houk*,Zhuangzhi Shi,* Nature, 2019. Accepted. [4] Ambimodal Trispericyclic Transition State and Dynamic Control of Periselectivity. Xiao-Song Xue,# Cooper S. Jamieson,# Marc Garcia-Borràs,# Xiaofei Dong,# Zhongyue Yang, K. N. Houk. J. Am. Chem. Soc. 2019. 141, 1217. (# equally contribution) [5] Chemodivergent and Stereoselective Construction of gem-Difluoroallylic Amines from Masked Difluorodiazo Reagents, Jun-Liang Zeng, Yue Zhang, Meng-Meng Zheng, Zhi-Qi Zhang, Xiao-Song Xue, Fa-Guang Zhang*, Jun-An Ma* Org. Lett., 2019, DOI: 10.1021/acs.orglett.9b02989. [6] Mechanisms and Dynamics of Reactions Involving Entropic Intermediates. Zhongyue Yang, Cooper S. Jamieson, Xiao-Song Xue, Marc Garcia-Borràs, Tyler Benton, Xiaofei Dong, Fang Liu, K. N. Houk. Trends in Chemistry, 2019. 1, 22. [7] Factors Controlling Reactivity in the Hydrogen Atom Transfer and Radical Addition Steps of a Radical Relay Cascade, Yike Zou, Xiao-Song Xue, Yifan Deng, Amos B Smith III, K. N Houk. Org. Lett., 2019. 21, 5894. [8] Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates, Feng Shen, Hanliang Zheng, Xiao-Song Xue, Long Lu, Qilong Shen, Org. Lett., 2019. 21, 6347-6351 [9] Chiral Spiro Phosphoric Acid-Catalyzed Friedel–Crafts Conjugate Addition/Enantioselective Protonation Reactions, Yi-Pan Li, Ziqi Li, Biying Zhou, Mao-Lin Li, Xiao-Song Xue, Shou-Fei Zhu, Qi-Lin Zhou, ACS Catal. 2019, 9, 6522-6529. [10] Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization, Quan-Qing Zhao, Man Li, Xiao-Song Xue*, Jia-Rong Chen*, Wen-Jing Xiao*, Org. Lett., 2019, 21, 3861-3865. [11] Computational I (III)―X BDEs for Benziodoxol (on)e‐based Hypervalent Iodine Reagents: Implications for their Functional Group Transfer Abilities, Jin-Dong Yang*, Man Li, Xiao-Song Xue*, Chin. J. Chem., 2019, 37, 359-363. [12] Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes, Biying. Zhou, Moriana K. Haj, Eric N. Jacobsen, Houk, K. N.,* Xiao-Song Xue,* J. Am. Chem. Soc. 2018, 140, 15206. [13] Exploration of the Synthetic Potential of Electrophilic Trifluoromethylthiolating and Difluoromethylthiolating Reagents. Jingjing Zhang; Yang Jin-Dong; Hanliang Zheng; Xue, Xiao-Song;* Herbert Mayr;* Jin-Pei Cheng. Angew. Chem. Int. Ed. 2018, 57, 12690. [14] Origins of Selectivities in the Stork Diels–Alder Cycloaddition for the Synthesis of (±)-4-Methylenegermine, Xiao-Song Xue, Levandowski, Brian J., Cyndi Qixin He, Houk, K. N.,* Org. Lett., 2018. 20, 6108. [15] Recent Advances and Advisable Applications of Bond Energetics in Organic Chemistry. Yang Jin-Dong, Ji Pengju, Xue Xiao-Song, Jin-Pei Cheng* J. Am. Chem. Soc. 2018. 140, 8611?8623. [16] Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes, Di Wang, Xiao-Song Xue, Kendall N. Houk,* and Zhuangzhi Shi.* Angew. Chem. Int. Ed. 2018, 16861. [17] Rhodium-Catalyzed 2-Arylphenol-Derived Six-Membered Silacyclization: Straightforward Access toward Dibenzooxasilines and Silicon-Containing Planar Chiral Metallocenes, Wen-Tao Zhao, Zhuo-Qun Lu, Hanliang Zheng, Xiao-Song Xue, Dongbing Zhao* ACS Catal.2018,89, 7997-8005 [18] Origin of Stereocontrol in Photoredox Organocatalysis of Asymmetric α-Functionalizations of Aldehydes. Li Man; Yueqian Sang; Xue, Xiao-Song;* Cheng, Jin-Pei. J. Org. Chem. 2018. 83, 3333. [19] A Systematic Theoretical Study on the Acidities for Cations of Ionic Liquids in Dimethyl Sulfoxide Wang Zhen; Zheng Yongjun; Zheng Yong; Xue, Xiao-Song;* Ji Pengju * J. Phys. Chem. A 2018, 122, 5750. [20] Acidity Scale of N-Heterocyclic Carbene Precursors: Can We Predict the Stability of NHC–CO2 Adducts? Zhen Wang, Fang Wang, Xiao-Song Xue,* Pengju Ji,* Org. Lett., 2018. 20, 6041. [21] Radical C–H Arylation of Oxazoles with Aryl Iodides: dppf as an Electron-Transfer Mediator for Cs2CO3 Zhengwei Guo; Man Li; Xue-Qing Mou; Gang He;* Xiao-Song Xue*; Gong Chen*. Org. Lett., 2018, 20, 1684. [22] Carbon-Selective Difluoromethylation of Soft Carbon Nucleophiles with Difluoromethylated Sulfonium Ylide, Jiansheng Zhu, Hanliang Zheng, Xiao-Song Xue*, Yisa Xiao, Yafei Liu, Qilong Shen,* Chin. J. Chem.2018. 36, 1069. [23] Computational Study of the Trifluoromethyl Radical Donor Abilities of CF3 Sources, Man, Li, Huiying, Kang, Xiao-Song Xue*, Jin-Pei, Cheng, Acta Chim. Sinica 2018, 76, 988-996. (Invited contribution) [24] Ordering the relative power of electrophilic fluorinating, trifluoromethylating, and trifluoromethylthiolating reagents: A summary of recent efforts. Li, Man; Zhen, Hanliang; Xue, Xiao-Song;* Cheng, Jin-Pei. Tetrahedron Lett. 2018, 59, 1278-1285. (Invited review) [25] Mechanism and Origins of Stereoinduction in Natural Cinchona Alkaloid Catalyzed Asymmetric Electrophilic Trifluoromethylthiolation of β-Ketoesters with N-Trifluoromethylthiophthalimide as Electrophilic SCF3 Source. Li, Man; Xue, Xiao-Song;* Cheng, Jin-Pei. ACS Catal., 2017, 7, 7977. [26] Establishing the Trifluoromethylthio Radical Donating Abilities of Electrophilic SCF3-Transfer Reagents. Li, Man; Zhou, Biying; Xue, Xiao-Song;* Cheng, Jin-Pei. J. Org. Chem. 2017. 82, 8697. [27] The Essential Role of Bond Energetics in C–H Activation/Functionalization, Xue, Xiao-Song;# Ji, Pengju,# Zhou, Biying; Cheng, Jin-Pei*. Chem. Rev. 2017, 117, 8622. (# equally contribution) [28] Hypervalent-Iodine-Mediated Formation of Epoxides from Carbon(sp2)–Carbon(sp3) Single Bonds. Shan Jiang, Tai-Shan Yan, Yong-Chao Han, Li-Qian Cui, Xiao-Song Xue,* Chi Zhang,* J. Org. Chem. 2017, 82, 11691. [29] N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C-H Hydrogen Bonding, Yao Li, Guo-Hui Yang, Ye-Ye Shen, Xiao-Song Xue, Xin Li*, Jin-Pei Cheng, J. Org. Chem. 2017, 82, 8662-8667. [30] “Design and Applications of N-tert-Butyl Sulfinyl Squaramide Catalysts.” Li, Yao; He, Qixin Cyndi; Gao, Fei-Xiang; Li, Zhen; Xue, Xiao-Song; Li, Xin;* Houk, K. N.;* Cheng, Jin-Pei. Org. Lett. 2017, 19, 1926. [31] “A Systematic Evaluation of the N-F Bond Strength of Electrophilic N-F Reagents: Hints for Atomic Fluorine Donating Ability.” Yang, Jin-Dong; Wang, Ya; Xue, Xiao-Song;* Cheng, Jin-Pei*. J. Org. Chem. 2017, 82, 4129. [32] “Sulfimine-Promoted Fast O Transfer: One–step Synthesis of Sulfoximine from Sulfide.”Xie, Yongtao; Zhou, Biying; Zhou, Sha; Zhou, Shaa; Wei, Wei; Liu, Jingbo; Zhan, Yizhou; Cheng, Dandan; Chen, Minggui; Li, Yuxin; Wang, Baolei; Xue, Xiao-Song; Li, Zhengming. ChemistrySelect 2017, 2, 1620. [33] “A Systematic Assessment of Trifluoromethyl Radical Donor Abilities of Electrophilic Trifluoromethylating Reagents.” Li, Man.; Wang, Ya; Xue, Xiao-Song;* Cheng, Jin-Pei. Asian J. Org. Chem. 2017. 6, 235. [34] “Theoretical study of Lewis acid activation models for hypervalent fluoroiodane reagent: The generality of “F-coordination” activation model.” Zhou, Biying; Xue, Xiao-Song;* Cheng, Jin-Pei. Tetrahedron Lett. 2017, 58,1287. [35] Origin of Stereoselectivity of the Photoinduced Asymmetric Phase Transfer-Catalyzed Perfluoroalkylation of beta-Ketoesters, Chen Yang, Wei Zhang, Yi-He Li, Xiao-Song Xue, Xin Li*, Jin-Pei Cheng, J. Org. Chem.2017, 82, 9321-9327. [36] “Mechanism of Silver-Mediated Geminal Difluorination of Styrenes with a Fluoroiodane Reagent: Insights into Lewis-Acid-Activation Model.” Zhou, Biying; Yan, Taishan.; Xue, Xiao-Song;* Cheng, Jin-Pei. Org. Lett. 2016, 18, 6128. [37] “Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para-Quinone Methides.” Dong, Nan; Zhang, Zhi. Pei; Xue, Xiao-Song; Li, Xin*; Cheng, Jin-Pei. Angew. Chem. Int. Ed. 2016, 55, 1460. [38] “Mechanism and Origin of Unexpected Chemoselectivity in Fluorocyclization of o-Styryl benzamides with a Hypervalent Fluoroiodane Reagent.” Yan, Taishan.; Zhou, Biying; Xue, Xiao-Song;* Cheng, Jin-Pei*. J. Org. Chem. 2016, 81, 9006. [39] “Quantitative Scale for the Trifluoromethylthio Cation-Donating Ability of Electrophilic Trifluoromethylthiolating Reagents.” Li, Man.; Guo, Jinping; Xue, Xiao-Song; * Cheng, Jin-Pei*. Org. Lett. 2016, 18, 264. [40] “An Energetic Guide for Estimating Trifluoromethyl Cation Donor Abilities of Electrophilic Trifluoromethylating Reagents: Computations of X–CF3 Bond Heterolytic Dissociation Enthalpies.” Li, Man.; Xue, Xiao-Song;* Guo, Jinping; Wang, Ya; Cheng, Jin-Pei*. J. Org. Chem. 2016, 81, 3119. [41] “Comprehensive Energetic Scale for Quantitatively Estimating the Fluorinating Potential of N–F Reagents in Electrophilic Fluorinations.” Xue, Xiao-Song; * Wang, Ya; Man, Li; Cheng, Jin-Pei*. J. Org. Chem. 2016, 81, 4280. [42] “N-Trifluoromethylthiodibenzenesulfonimide: A Shelf-Stable, Broadly Applicable Electrophilic Trifluoromethylthiolating Reagent.” Zhang, Panpan; Li , Man; Xue, Xiao-Song; * Xu, Chunfa; Zhao, Qunchao; Liu, Yafei; Wang, HaoYang; Guo, Yinlong; Lu, Long;* Shen, Qilong.* J. Org. Chem. 2016, 81, 7486. [43] “A Systematic Assessment of Trifluoromethyl Radical Donor Abilities of Electrophilic Trifluoromethylating Reagents.” Li, Man.; Wang, Ya; Xue, Xiao-Song;* Cheng, Jin-Pei. Asian J. Org. Chem. 2016, DOI: 10.1002/ajoc.201600539. [44] “Toward Prediction of the Chemistry in Ionic Liquids: An Accurate Computation of Absolute pKa Values of Benzoic Acids and Benzenethiols.” Xue, Xiao-Song; * Wang, Ya; Chen, Yang; Ji, Pengju, Cheng, Jin-Pei*. J. Org. Chem. 2015, 80, 8997. [45] “A Highly Efficient Chirality Switchable Synthesis of Dihydropyran-Fused Benzofurans by Fine-Tuning the Phenolic Proton of β-Isocupreidine (β-ICD) Catalyst with Methyl.” Wang, Feng; Yang, Chen.; Xue, Xiao-Song; Li, Xin.; * Cheng, Jin-Pei. * Chem. Eur. J. 2015, 21, 10443. [46] “A Computational Study on the pKa Shifts of Proline Induced by Hydrogen-bond Donating Co-catalysts.” Xue, Xiao-Song; Chen, Yang; Li, Xin;* Cheng, Jin-Pei*. J. Org. Chem. 2014, 79, 1166. [47] “Computational Study on the Acidic Constants of Chiral Br?nsted Acids in Dimethyl Sulfoxide” Chen, Yang; Xue, Xiao-Song; Li, Xin;* Cheng, Jin-Pei*. J. Org. Chem. 2014, 79, 4340. [48] “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.”Xue, Xiao-Song; Chen, Yang; Li, Xin; Cheng, Jin-Pei*. Org. Chem. Front. 2014, 1, 176. [49] “Mechanism and Selectivity of Bio-inspired Novel Cinchona Alkaloid Derivatives Catalyzed Asymmetric Olefin Isomerization: A Computational Study.” Xue, Xiao-Song; Li, Xin; Yu, Ao;* Chen, Yang; Song, Chan; Cheng, Jin-Pei*. J. Am. Chem. Soc. 2013, 135, 7462. [50] “Theoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis.” Yang, Chen; Xue, Xiao-Song; Jin, Jialu; Li, Xin*; Cheng, Jin-Pei*. J. Org. Chem. 2013, 78, 7076. [51] “Synthesis of Optically Enriched Spirocyclic Benzofuran-2-ones via Bifunctional Thiourea Catalyzed Double-Michael Addition of Benzofuran-2-ones to Dienones.” Li, Xin*; Yang, Chen; Jin, Jialu; Xue, Xiao-Song; Cheng, Jin-Pei*. Chem. Asian J. 2013, 8, 4. [52] “Enantioselective Organocatalyzed Sulfenylation of 3-Substituted Oxindoles.” Li, X;* Liu. Cong; Xue, Xiao-Song; Cheng, Jin-Pei*. Org. Lett. 2012, 4374. [53] “Asymmetric Michael Addition Reactions of 3-Substituted Benzofuran-2(3H)-ones to Nitroolefins Catalyzed by a Bifunctional Tertiary-amine thiourea.” Li, Xin;* Xue, Xiao-Song; Liu, Cong; Wang, Bin; Tan, Boxuan; Jin, Jialu; Zhang, Yueyan; Dong, Nan; Cheng, Jin-Pei*. Org. Biomol. Chem. 2012, 10, 413. [54] “The Effects of Insertion of Nitrogen Atoms on the Aromatic Nitrogen-Containing Compounds: a Potential Approach for Designing Stable Radical Molecular Materials.” Yu, Ao*; Xue, Xiao-Song; Wang, Jian.; Wang, Huikai.; Wang, Yongjian, J. Phys. Org. Chem. 2012, 25, 92. [55] “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.” Li, Xin*; Zhang, Yuanyan; Xue, Xiao-Song; Jin, Jialu; Tan, Boxuan; Liu, Cong; Dong, Nan; Cheng, Jin-Pei*. Eur. J. Org. Chem. 2012, 1774. [56] “Theoretical Study on the Thermodynamic Hydricity of Imidazole-based Organic Hydrides in Acetonitrile.” Yu, Ao;* Wang, Huikai; Xue, Xiao-Song; Cai, Yu.; Wang, Yongjian; He, Jiaqi. Chem. J. Chinese. U. 2012, 33, 276. [57] “A Computational Reinvestigation of the Formation of N-Alkylpyrroles via Intermolecular Redox Amination.” Xue, Xiao-Song; Yu, Ao;* Cai, Yu; Cheng, Jin-Pei. Org. Lett. 2011, 13, 6054. [58] “Organic Radicals Based on Phenalenyl and Verdazyl Units.” Hou, Yanhui;* Wang, Huikai; Li, Zhi; Liu, Yongshen; Wan, Xianjian; Xue, Xiao-Song; Chen, Yongsheng; Yu, Ao. Tetrahedron Lett. 2011, 52, 3670. [59] “The Rearrangement of 2-(1,6-Methano 10 annulenyl)-3,3-dimethylmethylenecyclopropane: A Computational Study.” Yu, Ao;* Xue, Xiao-Song; Wang, Jinjian; Wang, Yongjian*. Theochem-J. Mol. Struct. 2010, 950, 1. [60] “Theoretical Study of the Peripheral Disulfide Bridge Substituent Effects on the Antioxidant Properties of Naphthyridine Diol Derivatives.” Yu, Ao;* Wang, Jijian; Xue, Xiao-Song; Wang, Yongjian*. J. Phys. Chem. A. 2010, 114, 1008. [61] “Selective Tuning of the HOMO-LUMO Gap of Carbazole-Based Donor-Acceptor-Donor Compounds toward Different Emission Colors.” Zhang, Huaqiang; Wan, Xianjian; Xue, Xiao-Song; Li, Yanqin; Yu, Ao; Chen, Yongsheng*. Eur. J. Org. Chem. 2010, 1681. Professional Cultivation