Xu,Jiaxi

Promulgator：曹鼎Date：2023-11-21Hits：15

Xu, Jiaxi

Professor

College of Chemistry

Email:jxxu@buct.edu.cn
Office: 1105 Science and Technology Building
Lab: 1107 Science and Technology Building
Phones: 010-64435565


Research Interests

Organic and Organometallic Chemistry —Synthetic organic methodology development, Catalyst design and applications in asymmetric synthesis.

  • His research interests include synthetic methodology and related mechanism, stereochemistry and asymmetric catalysis. His research group developed synthetic methods of various substituted taurines, convergent synthesis of phosphonopeptides. He has been especially interested in the stereochemistry and formation mechanism in the synthesis of -lactams and -sultams from imines and ketenes or alkanesulfonyl chlorides via the Staudinger cycloaddition and sulfa-Staudinger cycloaddition. He revealed the origin of the diastereoselectivity in the Staudinger cycloaddition. He also elucidated the annuloselectivities (annulation selectivities between [2+2] annulation and [2+2+2] annulation) in the reactions of imines with ketenes or sulfenes or their equivalents and stereochemistry of [2+2+2] annulation. Currently, phostams, phostims, phostones, and phostines are interesting compounds in his research group.

  • Synthesis of new heterocycles and new methods for synthesis of biologically active heterocycles are the unifying theme of his group. Design and synthesis of new catalyst architectures and their applications in asymmetric transformations, especially for synthesis of medicinal intermediates, are also his objective.

Biography

Education & work experience

  • B.S. Peking University, Beijing, China (1983.9-1987.6)

  • Ph.D. Peking University, Beijing, China (1987.9-1992.7)

  • Postdoctoral Fellow, Beijing Medical University, Beijing, China (1992.7-1994.7)

  • Associate and full professor, Peking University, Beijing, China (1994.7-2007.10)

  • Visiting research associate, The Chinese University of Hong Kong, Hong Kong, China (1995.8-1996.1)

  • Postdoctoral Fellow, Colorado State University, CO & Vanderbilt University, TN, USA (2000.3-2002.1)

  • Professor, Beijing University of Chemical Technology, Beijing, China (2007.11-present)

Awards & honours

  • Outstanding Young Teachers Assistance Project (Ministry of Education) (2002)

  • Excellent Textbook for Universities (Grade B) (Ministry of Education) (2003)

  • Excellent Advisor for the National Undergraduates “Challenge Cup” (2006)

  • Excellent Professor in Beijing (2011)

  • Fulbright Scholarship Award (2012)

  • Teaching Achievement Award in Beijing (Grade A) (2013)

  • National Teaching Achievement Award (Grade B) (2014)

  • Teaching Achievement Award in Beijing (Grade A) (2017)

  • Teaching Achievement Award in Beijing (Grade B) (2017)

Projects & Funding

  • National Natural Science Foundation of China for International Joint Research Project (Grant No. 21911530099), ¥150000，2019.1-2020.12

  • National Natural Science Foundation of China for General Program (Grant No. 21772010), ¥640000，2018.1-2021.12; (Grant No. 21572017), ¥650000，2016.1-2019.12; (Grant No. 21372025), ¥800000，2014.1-2017.12; (Grant No. 21172017), ¥600000，2012.1-2015.12; (Grant No. 20972013), ¥350000，2010.1-2012.12; (Grant No. 20772005), ¥280000，2008.1-2010.12.

  • Beijing Natural Science Foundation, General Program (Grant No. 2092022), ￥200000, 2009.1-2011.12

  • National Basic Research Program of China (no. 2013CB328905) , ￥1950000, 2012.1-2015.12

  • National Key Research and Development Program of China, (Grant No. 2022YFF0709800), ￥2000000, 2022.10-2025.12

Selected Publications

  1. Sun, Simin; Wei, Yuliang; Xu, Jiaxi*. Difluorocarbene-triggered [1+5] annulation: Access to functionalized 1,1-difluoro-1,9a-dihydropyrido[2,1-c][1,4]thiazine derivatives. Org. Lett. 2023, 25(16), 2868–2872.

  2. Sun, Simin; Wei, Yuliang; Xu, Jiaxi*. Microwave-mediated stereocontrolled annulations of diazo(aryl)methyl(diaryl)phosphine oxides with pyridinium 1,4-zwitterionic thiolates. Chem. Commun. 2023, 59(2), 239–242.

  3. Yuan, Xin; Ke, Xuan; Xu, Jiaxi*. [2 + 4] Annulation of alkyl(phenyl)phosphinic chlorides with enones: Stereoselective synthesis of δ-phosphinolactones. Org. Lett. 2022, 24(49), 9141–9145.

  4. Sun, Simin; Wei, Yuliang; Xu, Jiaxi*. Visible-light-induced [1 + 5] annulation of phosphoryl diazomethylarenes and pyridinium 1,4-zwitterionic thiolates. Org. Lett. 2022, 24(32), 6024–6030.

  5. Sun, Simin; Zhang, Mengyao; Xu, Jiaxi*. Direct synthesis of highly strained bifunctionalized 2H-thiete 1,1-dioxides. Org. Chem. Front. 2022, 9(12), 3335–3341.

  6. Fu, Zhicheng; Lei, Yelong; Sun, Fang; Xu, Jiaxi*. Electrophilic hydrophosphonylation of aldimines with alkylphosphonochloridates provides access to (E)-alk-1-enylphosphonamidates. Org. Chem. Front. 2022, 9(9), 2464–2470.

  7. Wu, Qiuyue; Xu, Jiaxi*. Regio- and stereoselective synthesis of thiazoline derivatives via the thioketene-induced ring expansion of aziridines. Chem. Commun. 2022, 58(16), 2714–2717.

  8. Fu, Xingyang; Li, Xinyao; Xu, Jiaxi*. Synthesis of cis-β-phosphinolactams from phosphenes and imines. Org. Lett.2021, 23(22), 8733–8737.

  9. Yuan, Wenhao; Xie, Wenlai; Xu, Jiaxi*. Strong acid-catalyzed electrophilic ring expansion of oxetanes and sulfoxonium ylides. Mol. Catal. 2021, 510, 111687.

  10. Shi, Yi; Li, Siqi; Lu, Yang; Zhao, Zizhen; Li, Pingfan; Xu, Jiaxi*. Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides. Chem. Commun.2020, 56(14), 2131–2134.

  11. Fu, Duo; Dong, Jun; Du, Hongguang; Xu, Jiaxi*. Methanesulfinylation of benzyl halides with dimethyl sulfoxide. J. Org. Chem. 2020, 85(4), 2752–2758.

  12. Luo, Yun; Xu, Jiaxi*. Annulation of diaryl(aryl)phosphenes and cyclic imines to access benzo--phospholactams. Org. Lett. 2020, 22(20), 7780–7785.

  13. Li, Siqi; Shi, Yi; Li, Pingfan; Xu, Jiaxi*. Nucleophilic organic base DABCO-mediated chemospecific Meinwald rearrangement of terminal epoxides into methyl ketones. J. Org. Chem.2019, 84(7), 4443–4450.

  14. Chen, Xingpeng; Lin, Chao; Du, Hongguang; Xu, Jiaxi*. Efficient direct synthesis of aziridine-containing chiral tridentate ligands by the iminium-mediated self-ring opening reaction of enantiopure aziridines and salicylaldehydes. Adv. Synth. Catal. 2019, 361(7), 1647–1661.

  15. Dong, Jun; Du, Hongguang, Xu, Jiaxi*. Synthesis of functionalized thietanes via electrophilic carbene-induced ring expansion of thiiranes with sulfonium acylmethylides as carbene precursors. J. Org. Chem. 2019, 84(17), 10724–10739.

  16. Zhou, Bingnan; Dong, Jun; Xu, Jiaxi*. Safe, metal-free, and direct synthesis of dialkyl acylmethylidenehydroazine-1,1-dicarboxylates from dimethylsulfoxonium acylmethylides and dialkyl azodicarboxylates. Adv. Synth. Catal. 2019, 391(19), 4540–4548.

  17. Fu, Zhicheng; Sun, Simin; Yang, Anjian; Sun, Fang; Xu, Jiaxi*. Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and α,-unsaturated ketones through tandem Michael addition and cyclization. Chem. Commun. 2019, 55(87), 13124–13127.

  18. Liu, Jitian; Yang, Shiyi; Tang, Weiping; Yang, Zhanhui; Xu, Jiaxi. Iridium-catalyzed efficient reduction of ketones in water with formic acid as hydride donor at low catalyst loading. Green Chem. 2018, 20(9), 2118–2124.

  19. Yang, Shiyi; Tang, Weiping; Yang, Zhanhui; Xu, Jiaxi. Iridium-catalyzed highly efficient and site-selective deoxygenation of alcohols. ACS Catal. 2018, 8(10), 9320–9326.

  20. Fu, Zhicheng; Yuan, Wenhao; Chen, Ning; Yang, Zhanhui; Xu, Jiaxi. Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water. Green Chem. 2018, 20(19), 4484–4491.

  21. Xu, Chuangchuang; Xu, Jiaxi. Oxygenophilic Lewis acid-promoted synthesis of 2-arylindoles from anilines and cyanoepoxides in alcohol. J. Org. Chem.2018, 83(23), 14733–14742.

  22. Yang, Zhanhui; Xu, Wei; Wu, Qiuyue; Xu, Jiaxi. Aminoxidation of thiols to N-chloro-N-sulfonyl sulfinamides. J.Org. Chem. 2016, 81(7), 3051–3057.

  23. Mo, Shanyan; Xu, Chuangchuang; Xu, Jiaxi. Expeditious and convenient synthesis of polycyclic difluoroboron complexes of 2-oxoindoline-3-carboxamides by tandem reaction. Adv. Synth. Catal.2016, 358(11), 1767–1777.

  24. Yang, Zhanhui; He, Wei; Cheng, Baoxiang; Xu, Jiaxi. Stereochemistry and mechanistic insight in the [2k+2i+2i] annulations of ketenes and imines. J.Org. Chem. 2016, 81(11), 4506–4510.

  25. Zhang, Zhong; Du, Hongguang; Xu, Jiaxi; Li, Pingfan. Anti-Markovnikov rearrangement in sulfur mediated allylic C–H amination of olefins. Chem. Commun. 2016, 52(77), 11547-11550.

  26. Yang, Zhanhui; Chen, Ning; Xu, Jiaxi.* Substituent-controlled annuloselectivity and stereoselectivity in the sulfa-Staudinger cycloadditions. J.Org. Chem. 2015, 80(7), 3611–3620.

  27. Li, Xinyao; Jin, Xin; Xu, Jiaxi.* Annuloselectivity in reactions of diacyl dichlorides and imines: Combined experimental and theoretical studies. J.Org. Chem. 2015, 80(14), 6976–6985.

  28. Yang, Zhanhui; Xu, Jiaxi.* Synthesis of benzo-γ-sultams via the Rh-catalyzed aromatic C-H functionalization of diazosulfonamides. Chem. Commun.2014, 50(27), 3616–3618.

  29. Mo, Shanyan; Xu, Jiaxi. Chemospecific intramolecular Büchner reaction catalyzed by copper(II) acetylacetonate. ChemCatChem2014, 6(6), 1679–1683.

  30. Mo, Shanyan; Li, Xinhao; Xu, Jiaxi. In situ generated iodonium ylides as safe carbene precursors for the chemoselective intramolecular Buchner reaction. J. Org. Chem. 2014, 79(19), 9186–9195.

  31. Yang, Zhanhui; Xu, Jiaxi.* Insights on β-sultam ring formation in the sulfa-Staudinger reactions. J. Org. Chem. 2014, 79(21), 10703–10708.

  32. Li, Xinyao; Xu, Jiaxi. Annuloselectivity in cycloadditions of ketenes with imines：A DFT study. J. Org. Chem. 2013, 78(2), 347–355.

  33. Li, Xinyao; Xu, Jiaxi.* DFT and experimental exploration of intramolecular[2+2+2] cycloaddition of oxanorbornadienedicarboxylates and anologs. J. Org. Chem. 2013, 78(7), 3039–3047.

  34. Hou, Shili; Li, Xinyao, Xu, Jiaxi. Mechanistic insight into the formal [1,3]- migration in the thermal Claisen rearrangement. J. Org. Chem. 2012, 77(23), 10856–10869.

  35. Liang, Yong; Jiao, Lei; Zhang, Shiwei; Yu, Zhixiang*; Xu, Jiaxi.* New insights into the torquoselectivity of the Staudinger reaction. J. Am. Chem. Soc. 2009, 131(4), 1542–1549.

  36. He, Fengdan; Meng, Fanhua; Song, Xiuqing; Hu, Wenxiang; Xu, Jiaxi. First and convergent synthesis of hybrid sulfonophosphinopeptides, Org. Lett. 2009, 11(17), 3922–3925.

  37. Li, Bonan; Wang, Yikai; Du, Da-Ming; Xu, Jiaxi*. Notable and obvious ketene substituent-dependent effect of temperature on the stereoselectivity in the Staudinger reaction. J. Org. Chem.2007, 72(3), 990–997.

  38. Li, Bonan; Cai, Shuzong; Du, Da-Ming; Xu, Jiaxi*. Synthesis of phosphinopeptides via the Mannich ligation. Org. Lett. 2007, 9(12), 2257–2260.

  39. Hu, Libo; Zhu, Hui; Du, Da-Ming; Xu, Jiaxi*. Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines. J. Org. Chem. 2007, 72(12), 4543–4546.

  40. Jiao, Lei; Zhang, Qianfeng; Liang, Yong; Zhang, Shiwei; Xu, Jiaxi*. A versatile method for the synthesis of 3-alkoxycarbonyl -lactam derivatives. J. Org. Chem.2006, 71(2), 815–818.

  41. Jiao, Lei; Liang, Yong; Xu, Jiaxi*. Origin of the relative stereoselectivity of the -lactam formation in the Staudinger reaction. J. Am. Chem. Soc. 2006, 128(18), 6060–6069.

  42. Wang, Yikai; Liang, Yong; Jiao, Lei; Du, Da-Ming; Xu, Jiaxi*. Do reaction conditions affect the stereoselectivity in the Staudinger reaction? J. Org. Chem.2006, 71(18), 6983–6990.

  43. Liang, Yong; Jiao, Lei; Zhang, Shiwei; Xu, Jiaxi*. Microwave and photoirradiation-induced Staudinger reactions of cyclic imines and ketenes generated from α-diazoketones. A further investigation into the Stereochemical process. J. Org. Chem. 2005, 70(1), 334–337.

  44. Ma, Linge; Du, Daming; Xu, Jiaxi*. Rational tuning chelate size of bis-oxazoline ligands to improve enantioselectivity in the asymmetric aziridination of chalcones. J. Org. Chem.2005, 70 (24), 10155–10158.

  45. Xu, Jiaxi*; Ma, Linge; Jiao, Peng. Asymmetric aziridination of chalcones catalyzed by a novel backbone 1,8-bisoxazolinylanthracene (AnBOX)-bopper bomplex. Chem. Commun. 2004, (14), 1616–1617.

  46. Xu, Jiaxi*; Wei, Tiezheng; Zhang, Qihan. Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones. J. Org. Chem. 2004, 69(20), 6860–6866.

  47. Xu, Jiaxi*; Wei, Tiezheng; Zhang, Qihan. Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. non-catalytic borane reduction, a non-neglectable factor in reduction system. J. Org. Chem. 2003, 68(26), 10146–10151.



links：

Research Group

https://chemistry.buct.edu.cn/2015/0331/c1950a22972/page.htm