Hydrogen Radical Initiated 1, 2-Alkynyl Migration
- Corresponding author: Tu Shu-Jiang, laotu@jsnu.edu.cn Jiang Bo, jiangchem@jsnu.edu.cn
Citation: Zhao Qi, Tu Shu-Jiang, Jiang Bo. Hydrogen Radical Initiated 1, 2-Alkynyl Migration[J]. Acta Chimica Sinica, ;2019, 77(9): 927-931. doi: 10.6023/A19040151
(a) Wu, X.; Wu, S.; Zhu, C. Tetrahedron Lett. 2018, 59, 1328; (b) Wu, X.; Zhu, C. Chin. J. Chem. 2019, 37, 171; (c) Li, W.; Xu, W.; Xie, J.; Yu, S.; Zhu, C. Chem. Soc. Rev. 2018, 47, 654.
(a) Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Tu, Y.-Q.; Zhang, F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781. (b) Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962. (c) Egami, H.; Shimizu, R.; Usui, Y.; Sodeoka, M. Chem. Commun. 2013, 49, 7346. (d) Chen, Z.-M.; Zhang, Z.; Tu, Y.-Q.; Xu, M.-H.; Zhang, F.-M.; Li, C.-C.; Wang, S.-H. Chem. Commun. 2014, 50, 10805. (e) Chu, X.-Q.; Zi, Y.; Meng, H.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2014, 50, 7642. (f) Mi, X.; Wang, C.; Huang, M.; Wu, Y.; Wu, Y. Org. Biomol. Chem. 2014, 12, 8394. (g) Chu, X.-Q.; Meng, H.; Zi, Y.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2014, 50, 9718. (h) Li, Y.; Liu, B.; Li, H.-B.; Wang, Q.; Li, J.-H. Chem. Commun. 2015, 51, 1024. (i) Song, R.-J.; Tu, Y.-Q.; Zhu, D.-Y.; Zhang, F.-M.; Wang, S.-H. Chem. Commun. 2015, 51, 749. (j) Zhao, J.; Fang, H.; Song, R.; Zhou, J.; Han, J.; Pan, Y. Chem. Commun. 2015, 51, 599.
(a) Wu, Z.; Ren, R.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 10821. (b) Wang, N.; Li, L.; Li, Z.-L.; Yang, N.-Y.; Guo, Z.; Zhang, H.-X.; Liu, X.-Y. Org. Lett. 2016, 18, 6026. (c) Ji, M.; Wu, Z.; Yu, J.; Wan, X.; Zhu, C. Adv. Synth. Catal. 2017, 359, 1959. (d) Ren, R.; Wu, Z.; Huan, L.; Zhu, C. Adv. Synth. Catal. 2017, 359, 3052.
Li, Z. L.; Li, X. H.; Wang, N.; Yang, N. Y.; Liu, X. Y. Angew. Chem., Int. Ed. 2016, 55, 15100.
doi: 10.1002/anie.201608198
(a) Wu, Z.; Wang, D.; Liu, Y.; Huan, L.; Zhu, C. J. Am. Chem. Soc. 2017, 139, 1388. (b) Gu, L. J.; Gao, Y.; Ai, X. H.; Jin, C.; He, Y. H.; Li, G. P.; Yuan, M. L. Chem. Commun. 2017, 53, 12946. (c) He, Y.; Wang, Y.; Gao, J.; Zeng, L.; Li, S.; Wang, W.; Zheng, X.; Zhang, S.; Gu, L.; Li, G. Chem. Commun. 2018, 54, 7499. (d) Wang, H.; Xu, Q.; Yu, S. Org. Chem. Front. 2018, 5, 2224. (e) Wang, M.; Wu, Z.; Zhang, B.; Zhu, C. Org. Chem. Front. 2018, 5, 1896. (f) Wei, X.-J.; No l, T. J. Org. Chem. 2018, 83, 11377. (g) Zhang, H.; Wu, X.; Zhao, Q.; Zhu, C. Chem.-Asian J. 2018, 13, 2453. (h) Zhang, W.; Zou, Z.; Wang, Y.; Wang, Y.; Liang, Y.; Wu, Z.; Zheng, Y.; Pan, Y. Angew. Chem., Int. Ed. 2019, 58, 624. (i) Zheng, M.-W.; Yuan, X.; Cui, Y.-S.; Qiu, J.-K.; Li, G.; Guo, K. Org. Lett. 2018, 20, 7784.
(a) Tang, X.; Studer, A. Angew. Chem., Int. Ed. 2018, 57, 814. (b) Gao, Y. Y.; Mei, H. B.; Han, J. L.; Pan, Y. Chem.-Eur. J. 2018, 24, 17205.
(a) Xu, Y.; Wu, Z.; Jiang, J.; Ke, Z.; Zhu, C. Angew. Chem., Int. Ed. 2017, 56, 4545. (b) Tang, X.; Studer, A. Chem. Sci. 2017, 8, 6888. (c) Liu, J.; Li, W. P.; Xie, J.; Zhu, C. J. Org. Chem. Front. 2018, 5, 797.
(a) Campbell, M. J.; Pohlhaus, P. D.; Min, G.; Ohmatsu, K.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 9180. (b) Alabugin, I. V.; Gilmore, K.; Manoharan, M. J. Am. Chem. Soc. 2011, 133, 12608.
Zhao, Q.; Ji, X.-S.; Gao, Y.-Y.; Hao, W.-J.; Zhang, K.-Y.; Tu, S.-J.; Jiang, B. Org. Lett. 2018, 20, 3596.
doi: 10.1021/acs.orglett.8b01382
(a) Bai, X.-Y.; Wang, Z.-X.; Li, B.-J. Angew. Chem., Int. Ed. 2016, 55, 9007. (b) Bai, X.-Y.; Zhang, W.-W.; Li, Q.; Li, B.-J. J. Am. Chem. Soc. 2018, 140, 506. (c) Chen, Y.; Wang, Z.-X.; Li, Q.; Xu, L.-J.; Li, B.-J. Org. Chem. Front. 2018, 5, 1815.
(a) Nishimura, T.; Katoh, T.; Takatsu, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14158. (b) Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 5060. (c) Canterbury, D. P.; Micalizio, G. C. J. Am. Chem. Soc. 2010, 132, 7602. (d) Avocetien, K. F.; Li, J. J.; Liu, X.; Wang, Y.; Xing, Y.; O'Doherty, G. A. Org. Lett. 2016, 18, 4970. (e) Teng, H.-L.; Ma, Y.; Zhan, G.; Nishiura, M.; Hou, Z. ACS Catal. 2018, 8, 4705.
Lo, J. C. L.; Gui, J. H.; Yabe, Y. K.; Pan, C. M.; Baran, P. S. Nature 2014, 516, 343.
doi: 10.1038/nature14006
(a) Lo, J. C.; Yabe, Y.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 1304. (b) Gui, J. H.; Pan, C. M.; Jin, Y.; Qin, T.; Lo, J. C.; Lee, B. J.; Spergel, S. H.; Mertzman, M. E.; Pitts, W. J.; La Cruz, T. E.; Schmidt, M. A.; Darvatkar, N.; Natarajan, S. R.; Baran, P. S. Science 2015, 348, 886. (c) Dao, H. T.; Li, C.; Michaudel, Q.; Maxwell, B. D.; Baran, P. S. J. Am. Chem. Soc. 2015, 137, 8046. (d) Zheng, J.; Wang, D.; Cui, S. Org. Lett. 2015, 17, 4572. (e) Zheng, J.; Qi, J.; Cui, S. Org. Lett. 2016, 18, 128. (f) Shen, Y.; Qi, J.; Mao, Z.; Cui, S. Org. Lett. 2016, 18, 2722. (g) Qi, J.; Zheng, J.; Cui, S. Org. Chem. Front. 2018, 5, 222. (h) Qi, J.; Zheng, J.; Cui, S. Org. Lett. 2018, 20, 1355. (i) Deng, Z.; Chen, C.; Cui, S. RSC Adv. 2016, 6, 93753.
Shen, Y.; Huang, B.; Zheng, J.; Lin, C.; Liu, Y.; Cui, S. Org. Lett. 2017, 19, 1744.
doi: 10.1021/acs.orglett.7b00499
CCDC 1913020(3e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO2 methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C60-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO4−, ReO4−). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn2+ doped quasi-two-dimensional perovskites (PEA)2PbyMn1-yBr4. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034
Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246