2、Metal-free, Direct Acylation of Purines to Access C6-Acylated Purines Derivatives Induced by TBHP via Minisci-type Reaction
Chunhui Zou, Mingwu Yu*, Zhongkai Jiang, Xiguang Liu,* Yiwen Chen, Lele Zhang
New Journal of Chemistry. 2024, 48, 5167-5172
A metal-free C-H functionalization of purines with aldehydes was developed to access C6-acylated purines via the green radical reactions. Theoretically, there are many competitive reactions due to three C-H bonds (C2-H, C6-H, C8-H) in the purine, the acylation only happened at purinyl C6 position. This method avoids metal catalyst and provides a green approach to construct C-C (sp2) bonds at purinyl C6-position, while maintaining excellent compatibility with various functional groups. Moreover, the protocol features broad substrate scopes and easy scale-up. The transformation of the product demonstrates the significant practical value of the method. The primary mechanism was proposed based on controlled experiments.
https://pubs.rsc.org/en/content/articlelanding/2024/nj/d3nj05712g/unauth
1、Metal-free, Late-stage Nitration Strategy to Construct 6-(ortho-nitroaryl)Amino Purine Derivatives Enabled by t-BuONO
Yiwen Chen, Jianhui Liu, Xiguang Liu,* Zhongkai Jiang, Shaorong Wang, Yixing Zhang, Mingwu Yu*
Tetrahedon Letters. 2024, 137, 154959
A late-stage, green and practical preparation of 6-(ortho-nitroaryl) amino purine derivatives was reported by using t-BuONO as the nitrating agent without transition-metal catalysts under air conditions. This method tolerates a wide variety of functional groups and is applicable for the gram scale synthesis, which may prove instrumental for further application in biochemistry. Preliminary mechanism was proposed through a series of experiments.
https://www.sciencedirect.com/science/article/abs/pii/S0040403924000534
J. Heterocyclic. Chem. 2023, 60, 1179-1189（SCI三区）
A metal-, light-free radical alkylation reaction of purines and nucleosides has been achieved with readily available alcohols (1o, 2o, 3o) as the alkyl radical sources enabled by oxalates, which does not need any catalysts, N2 protection and protecting groups.
Qingsong Jiang, a Xiguang Liu,*a Weili Wang, a Yiwen Chen a and Mingwu Yu*a
Org. Biomol. Chem. 2023, 21, 1744-1754（SCI二区）
The highly C6-regioselective alkylation of purines and purine nucleosides via oxidative homolysis of 4-alkyl-1,4-dihydropyridines at room temperature without metal catalysts and additional acid are first reported.
Mingwu Yu,a* Qingsong Jiang,a Xiguang Liu,a* Yiwen Chen,a Kai Sunb, Miao Tian,b* and Weili Wanga
1、Metal-free, Light-mediated, Site-specific, Radical C6-H Alkylation of Purines with Alcohols Intervened by Oxalates without Catalysts
Gang Liu,a Xianfeng Mu,a Miao Tian,b Weili Wang,a Chunhui Zou,aYiwen Chen,a Mingwu Yu*
Eur. J. Org. Chem. 2023, 26, e202201491（封面论文）
Herein, we report the development of a radical deoxy-functionalization strategy for the direct C-H alkylation of purines and purine nucleosides with alcohols (1o, 2o, 3o) intervened by oxalates under 12 W blue LED irradiation.
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202201491
Expeditious highly C6-regioselective acylation of purines and purine nucleosides via proton traceless aided at room temperature without metal catalyst are first reported.
https://pubs.rsc.org/en/content/articlelanding/2022/qo/d2qo00712f
1、Regioselective C6−H Hydroxyalkylation of Purines and Purine Nucleosides via α‑C−H Functionalization of Alcohols at Room Temperature
Mingwu Yu,a* Zheng Zhou,a Yiwen Chen,a Zhichuan Wang, bWeili Wang,aand Kai Sunb*
Org. Lett., 2022, 24, 4886-4891. (SCI一区TOP)
The highly regioselective C6–H hydroxylalkylation of purines and purine nucleosides within 10 min via the α-C(sp3)–H functionalization of alcohols at room temperature is reported here for the first time.
https://pubs.acs.org/doi/10.1021/acs.orglett.2c01680?ref=PDF
该论文被国际知名化学评论期刊亮点评述：Synfacts 2022; 18(10): 1072
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0042-1752977
2021年
A Facile approach to [1,2,4]triazolo[3,4-i]purine via PIDA oxidation ring-closing reaction
Xiangbin Suna, Mingwu Yua*, Xianfeng Mua, Zheng Zhoua, Linqing Wanga, Jianhui, Liuc, Xiguang Liub*
J. Heterocyclic. Chem., 2021, 58, 2270-2279 (SCI 三区)
A facile oxidative conversion of 6-(2-arylidenehydrazineyl) purines to [1,2,4] triazolo [3,4-i] purines using PhI(OAc)2 in only 10 minutes under room temperature is presented.
https://onlinelibrary.wiley.com/doi/abs/10.1002/jhet.4351
2018年
Expeditious synthesis of 9-allenylpurines via cesium carbonate catalyzed isomerization of 9-alkynylpurines
Mingwu Yua*, Xiguang Liua, Qingsong Jianga, Hongguang Dub.
Phosphorus Sulfur. 2018, 193, 451-458. (SCI 四区)
An expeditious and convenient method to synthesize 9-allenylpurines via cesium carbonate catalyzed isomerization of 9-alkynylpurines has been successfully developed.
https://www.tandfonline.com/doi/full/10.1080/10426507.2018.1436547
2016年
Mingwu Yu, Zhiqian Wang, Miao Tian, Chenghu Lu, Shunlai Li, and Hongguang Du*
J. Org. Chem. 2016, 81, 8, 3435–3442. (SCI 二区TOP)
https://doi.org/10.1021/acs.joc.5b01360
2015年
Mingwu Yu, Zhiqian Wang, Junbin Hu, Shunlai Li, and Hongguang Du*
J. Org. Chem. 2015, 80, 19, 9446–9453. (SCI二区TOP)
https://doi.org/10.1021/acs.joc.6b00148
