薛小松
薛小松
博士 副教授
薛小松,博士,副教授,化学系,毕业于南开大学,重庆市南川区人。
工作内容:教学科研
特殊人才称号:2016年入选天津市“131”创新型人才第三层次
通讯地址:天津市卫津路94号 南开大学 六教318室
电 话:
电子邮件:xuexs@nankai.edu.cn
课题组网站:https://poc.nankai.edu.cn/info/1020/1016.htm
研究领域:

物理有机化学,计算化学:1)化学反应机理与规律;2)功能分子的结构-活性关系;3理论与计算有机化学。

教育及科研经历:

2013年获南开大学博士学位(师从程津培院士)

2010年8-10月在北京大学余志祥课题组交流学习

2017年9-2020年8月,在美国University of California, Los Angeles 美国科学院院士Ken N Houk教授课题组访问学者

荣誉和奖励
南开大学优秀博士毕业生
科研成果与代表作

部分发表文章:

[1] Establishing for Cation and Radical Donor Ability Scales of Electrophilic F, CF3, and SCF3 transfer reagents, Man Li, Xiao-Song Xue*, Jin-Pei Cheng, Acc. Chem. Res. 2020, 53, 182−197. (Invited review)

[2] Radical-Mediated CC Cleavage of Unstrained Cycloketones and DFT Study for Unusual Regioselectivity, Mingyang Wang, Man Li, Shan Yang, Xiao-Song Xue*, Xinxin Wu & Chen Zhu*, Nat Commun. 2020, 11, 672.

[3] Quantification of the Activation Capabilities of Lewis/Brønsted Acid for Electrophilic Trifluoromethylthiolating Reagents, Huiying Kang, Biying Zhou, Li Man, Xiao-Song Xue*, Jin-Pei Cheng, Chin. J. Chem. 2020, 38, 130-134. (Invited contribution)

[4] Polarity Umpolung Strategy for the Radical Alkylation of Alkenes, Jige Liu, Shuo Wu, Jiajia Yu  Chenxi Lu, Zhen Wu, Xinxin Wu, Xiao-Song Xue, Chen Zhu*, Angew. Chem. Int. Ed. 2020, 59, 8195 -8202.

[5] Comprehensive Basicity Scales for N‐Heterocyclic Carbenes in DMSO: Implications on the Stabilities of N‐Heterocyclic Carbene and CO2 Adducts, Zhen Wang*, Xiao-Song Xue, Yanhua Fu, Pengju Ji* Chem. Asian J. 2020, 15,169-181

[6] Recent Computational Studies on Mechanisms of Hypervalent Iodine(III)-Promoted Dearomatization of Phenols, Hanliang Zheng, Xiao-Song Xue* Current Organic Chemistry, 2020, 4, 1. (Invited contribution)

[7] 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. 141, 16046-16056.

[8] Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation. Honggui Lv, Huiying Kang, Biying Zhou, Xiao-Song Xue,* Keary Engle,* and Dongbing Zhao*, Nat Commun. 2019, 10, 5025.

[9] 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, 11, 948–956. (# equally contribution)

[10] 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. 575, 336-340.

[11] 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)

[12] Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles, Zhi-Qi Zhang, Meng-Meng Zheng, Xiao-Song Xue, Ilan Marek,* Fa-Guang Zhang,* Jun-An Ma, Angew.Chem. Int .Ed. 2019, 58,18191-18196.

[13] 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, 21, 8244-8249.

[14]  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.

[15]  Expanding the Frontiers of Higher-Order Cycloadditions, David McLeod, Mathias Kirk Thøgersen, Nicolaj Inunnguaq Jessen, Karl Anker Jørgensen, Cooper S. Jamieson, Xiao-Song Xue, K. N. Houk,* Fang Liu,*, and Roald Hoffmann, Acc. Chem. Res. 2019, 52, 3488−3501.

[16]  Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process, Gabrielle H. Lovett, Shuming Chen, Xiao-Song Xue, K. N. Houk,* David W. C. MacMillan,* J. Am. Chem. Soc. 2019, 141, 51, 20031-20036.

[17]  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.

[18]  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

[19]  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.

[20]  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.

[21]  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. (Invited contribution)

[22]  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.

[23]  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.

[24]  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.

[25]  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.

[26]  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.

[27]  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

[28]  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.

[29]  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.

[30]  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.

[31]  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.

[32]  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.

[33]  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)

[34]  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)

[35]  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.

[36]  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.

[37]  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)

[38]  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.

[39]  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.

[40]  “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.

[41]  “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.

[42]  “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.

[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. 2017. 6, 235.

[44]  “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.

[45]  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.

[46]  “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.

[47]  “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.

[48]  “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.

[49]  “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.

[50]  “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.

[51]  “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.

[52]  “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.

[53]   “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.

[54]  “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.

[55]  “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.

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

[57]  “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.

[58]  “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.

[59]  “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.

[60]  “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.

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

[62]  “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.

[63]  “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.

[64]  “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.

[65]  “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.

[66]  “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.

[67]  “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.

[68]  “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.

[69]  “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.

[70] “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.

人才培养

教师办公管理系统 维护系统 会议室预约系统 院级仪器管理平台 化学学院论文评审系统