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【1st.Dec.】Selective, Three-component Dicarbofunctionalization of Unactivated Alkenes via Nickel Catalysis

2020-11-30

题目:Selective, Three-component Dicarbofunctionalization of Unactivated Alkenes via Nickel Catalysis
报告人:储玲玲 研究员,博士生导师,东华大学
时间:12月1日下午1:30-5:00
地点:化学B楼410会议室
邀请人:张兆国教授

个人简历



储玲玲 研究员, 本科,合肥工业大学,博士,中国科学院上海有机化学研究所(导师:卿凤翎 研究员),研究助理,中国科学院上海有机化学研究所,博士后,普林斯顿大学(导师:David MacMillan 教授),2016.9至今 研究员,博士生导师,东华大学
获得奖励和荣誉
2020    上海市“科技创新行动计划”启明星项目
2020    上海市第十一届巾帼创新新秀奖及上海市三八红旗手
2019    国家自然科学二等奖 (排名第二)
2017    上海市自然科学一等奖 (排名第二)
2017    上海市青年科技英才扬帆计划
2012    中科院优秀博士论文
社会兼职
1. Science Bulletin 青年编委
2. 中国化学会青年委员会委员
研究兴趣与方向 
光促自由基化学,镍催化选择性转化,有机含氟材料


近三年代表性成果
1. Guo, L.;# Yuan, M.;# Zhang,Y.; Wang, F.; Zhu, S. Gutierrez, O.,* Chu, L.*, “Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins Through Nickel-Catalyzed Cross-Electrophile Coupling”, J. Am. Chem. Soc. 2020, DOI: 10.1021/jacs.0c08823.
2. Yang, J.;# Zhu, S.;# Wang, F.; Qing, F,; Chu, L.*, “Silver-Enabled General Radical Difluoromethylation Reaction with TMSCF2H”, Angew. Chem. Int. Ed. 2020, DOI: 10.1002/anie.202014587.
3. Tu, H.-Y.;# Wang, F.;# Huo, L.; Li, Y.; Zhu, S.; Zhao, X.; Li, H.; Qing, F.-L.; Chu, L.*, “Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins Through Nickel-Catalyzed Cross-Electrophile Coupling”, J. Am. Chem. Soc. 2020, 142 (21), 9604–9611.
4. Song, F.;# Wang, F.;# Guo, L.; Feng, X.-L.; Zhang, Y.-Y.; Chu, L.*, “Visible-Light-Enabled Stereodivergent Synthesis of (E)- and (Z)-1,4-Dienes via Photoredox/Nickel Dual Catalysis”, Angew. Chem. Int. Ed. 2020, 59 (1), 177-181. (Hot Paper)
5. Li, H;# Guo, L.;# Feng, X.; Huo, L.; Zhu, S.; Chu, L.*, “Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins Through Nickel-Catalyzed Cross-Electrophile Coupling”, Chem. Sci. 2020, 11, 4904-4910.
6. Guo, L.#; Tu, H.-Y. #; Zhu, S.; Chu, L.*, “Selective, Intermolecular Alkylarylation of Alkenes via Photoredox/Nickel Dual Catalysis”, Org. Lett. 2019, 21, 4771-4776.
7. Zhu, S.; Qin, J.; Wang, F.; Li, H.; Chu, L.*, “Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine”, Nat. Commun. 2019, 10, 749.
8. Chen, D.; Xu, L.; Long, T.; Zhu, S.; Yang, J.; Chu, L.*, “Metal-free, intermolecular carbopyridylation of alkenes via visible-light-induced reductive radical coupling”, Chem. Sci. 2018, 9, 9012-9017.
9. Guo, L.; Song, F.; Zhu, S.; Li, H.; Chu, L.*, “syn-Selective Alkylarylation of Terminal Alkynes via the Combination of Photoredox and Nickel Catalysis” Nat. Commun., 2018, 9, 4543.
10. Zhao, X.#; Tu, H.-Y.#; Guo, L.; Zhu, S.; Qing F.-L.; Chu, L.*, “Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay” Nat. Commun., 2018, 9, 3488.

报告摘要


Selective, Three-component Dicarbofunctionalization of Unactivated Alkenes via Nickel Catalysis
Lingling Chu (储玲玲) 
1Center for Advanced Low-dimension Materials, Donghua University, Shanghai, 201610 E-mail: lingling.chu1@dhu.edu.cn


Transition metal-catalyzed dicarbofunctionalization of alkenes has been proven as a powerful strategy to the rapid generation of molecular complexity by simultaneously forging two vicinal sp3 C–C bonds from abundant building blocks in one single operation; however, selective control, particularly with enantioselective control, of the newly formed stereogenic centers in three-component assembly mode, remains a formidable challenge. Utilizing a nickel-catalyzed radical cascade strategy, we have developed a series of intermolecular, three-component dicarbofunctionalization of unactivated alkenes with excellent selectivity under mild conditions, allowing for facile excess to a wide range of highly functionalized fluoroalkyl-containing molecules from simple starting materials.


 
Fig. 1. Ni-catalyzed three-component dicarbofunctionalization reactions




References:
[1] Guo, L.;# Yuan, M.;# Zhang,Y.; Wang, F.; Zhu, S. Gutierrez, O.,* Chu, L.*, “J. Am. Chem. Soc. 2020, DOI: 10.1021/jacs.0c08823.
[2] Tu, H.-Y.;#, Wang, F.; # Huo, L.; Li, Y.; Zhao, X.; Li, H.; Qing F.-L.; Chu, L.*, J. Am. Chem. Soc. 2020, 142, 9604.
[3] Song, F.;# Wang, F.;# Guo, L.; Feng, X.-L.; Zhang, Y.-Y.; Chu, L.*, Angew. Chem. Int. Ed. 2020, 59, 177-181.
[4] Li, H.;# Guo, L.;# Feng, X.-L.; Huo, L.-P.; Zhu, S.-Q.;; Chu, L.*, Chem. Sci. 2020, 11, 4904-4910.
[5] Guo, L.; # Tu, H.-Y. #; Zhu, S.; Chu, L.*, Org. Lett. 2019, 21, 4771.
[6] Guo, L.; Song, F.; Zhu, S.; Li, H.; Chu, L.*, Nat. Commun., 2018, 9, 4543.
[7] Zhao, X.#; Tu, H.-Y.#; Guo, L.; Zhu, S.; Qing F.-L.; Chu, L.*, Nat. Commun., 2018, 9, 3488.




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