Iodine-mediated regioselective hydroxyselenenylation of alkenes: Facile access to β-hydroxy selenides
- Corresponding author: Yan Jie, jieyan87@zjut.edu.cn
Citation:
Wang Xian-Long, Li Hong-Jie, Yan Jie. Iodine-mediated regioselective hydroxyselenenylation of alkenes: Facile access to β-hydroxy selenides[J]. Chinese Chemical Letters,
;2018, 29(3): 479-481.
doi:
10.1016/j.cclet.2017.06.023
R.M. Romero, T.H. Woste, K. Muniz, Chem.-Asian J. 9(2014) 972-983.
doi: 10.1002/asia.v9.4
E.M. Beccalli, G. Broggini, S. Gazzola, et al., Org. Biomol. Chem. 12(2014) 6767-6789.
doi: 10.1039/C4OB00610K
B. Zhao, X. Peng, Y. Zhu, et al., J. Am. Chem. Soc. 133(2011) 20890-20900.
H.W. Zhang, Y.C. Song, J.B. Zhao, et al., Angew. Chem., Int. Ed. 53(2014) 11079-11083.
doi: 10.1002/anie.201406797
C. Chen, M.B. Hecht, A. Kavara, et al., J. Am. Chem. Soc. 137(2015) 13244-13247.
doi: 10.1021/jacs.5b08611
K.B. Sharpless, R.F. Lauer, J. Am. Chem. Soc. 95(1973) 2697-2699.
doi: 10.1021/ja00789a055
H.J. Reich, F. Chow, J. Chem. Soc., Chem. Commun. 3(1975) 790-791.
M. Sevring, W. Dumont, L. Hevesi, et al., Tetrahedron Lett. 17(1976) 2647-2650.
doi: 10.1016/S0040-4039(00)91758-1
D. Van Ende, W. Dumont, A. Krief, Angew Chem. Int. Ed. Engl. (1975) 700-702.
W. Dumont, A. Krief, Angew. Chem. Int. Ed. Engl. (1975) 350-351.
J.H. Rigby, U.S.M. Maharoof, M.E. Mateo, J. Am. Chem. Soc. 122(2000) 6624-6628.
doi: 10.1021/ja000930i
E.M. Treadwell, J.D. Neighbors, D.F. Wiemer, Org. Lett. 4(2002) 3639-3642.
doi: 10.1021/ol0266368
S. Knapp, D.L. Zhao, Org. Lett. 2(2000) 4037-4040.
doi: 10.1021/ol0066680
A. Toshimitsu, T. Aoai, H. Owada, et al., Tetrahedron 41(1985) 5301-5306.
doi: 10.1016/S0040-4020(01)96781-X
A. Toshimitsu, T. Aoai, H. Owada, et al., J. Chem. Soc., Chem. Commun. (1980) 412-413.
M. Tingoli, R. Diana, B. Panunz, Tetrahedron Lett. 47(2006) 7529-7531.
doi: 10.1016/j.tetlet.2006.08.068
K.C. Nicolaou, D.A. Claremon, W.E. Barnette, et al., J. Am. Chem. Soc. 101(1979) 3704-3706.
doi: 10.1021/ja00507a069
M. Yoshshida, S. Sasage, K. Kawamura, et al., Bull. Chem. Soc. Jpn. 64(1991) 416-422.
doi: 10.1246/bcsj.64.416
M. Tiecco, L. Testaferri, A. Temperini, Synlett (2001) 1767-1771.
M. Tingoli, M. Tiecco, L. Testaferri, et al., Synth. Commun. 28(1998) 1769-1778.
doi: 10.1080/00397919808007007
S. Torii, K. Uneyama, M. Ono, Tetrahedron Lett. 21(1980) 2741-2744.
doi: 10.1016/S0040-4039(00)78594-7
S.V. Ley, L.A. O'Neil, C.M.R. Low, Tetrahedron 42(1986) 5363-5368.
doi: 10.1016/S0040-4020(01)82086-X
S. Berlin, C. Ericsson, L. Engman, J. Org. Chem. 68(2003) 8386-8396.
doi: 10.1021/jo030153f
B. Movassagh, S. Farshbaf, Synthesis (2010) 33-35.
M. Sakakibara, K. Katsumata, Y. Watanabe, et al., Synthesis (1992) 377-379.
V. Ganesh, C. Srinivasan, Synthesis (2009) 3267-3278.
L. Min, G. Wu, M.C. Liu, et al., J. Org. Chem 81(2016) 7584-7590.
doi: 10.1021/acs.joc.6b01274
R.D. Richardson, T. Wirth, Angew Chem. Int. 45(2006) 4402-4404.
doi: 10.1002/(ISSN)1521-3773
J. Feng, S. Liang, S.Y. Chen, et al., Adv. Synth. Catal. 354(2012) 1287-1292.
doi: 10.1002/adsc.201100920
K. Yang, M. Ke, Y.G. Lin, Green Chem. 17(2015) 1395-1399.
doi: 10.1039/C4GC02236J
Y.N. Duan, Z. Zhang, C. Zhang, Org. Lett. 18(2016) 6176-6179.
doi: 10.1021/acs.orglett.6b03209
S. Ambethkar, M. Vellimalai, V. Padmini, et al., New J. Chem. 41(2017) 75-80.
doi: 10.1039/C6NJ02102F
H.W. Shi, C. Yu, M. Zhu, et al., J. Organomet. Chem. 776(2015) 117-122.
doi: 10.1016/j.jorganchem.2014.10.025
H.W. Shi, C. Yu, J. Yan, Chin. Chem. Lett. 26(2015) 1117-1120.
doi: 10.1016/j.cclet.2015.05.029
C. Yu, H.W. Shi, M. Zhu, et al., Synlett 26(2015) 2139-2144.
doi: 10.1055/s-00000083
Y.K. Zhang, S.X. Wu, J. Yan, Helv Chim. Acta 99(2016) 654-658.
doi: 10.1002/hlca.201600115
C. Muangkaew, P. Katrun, P. Kanchanarugee, et al., Tetrahedron 69(2013) 8847-8856.
doi: 10.1016/j.tet.2013.08.018
Z.Z. Huang, X. Huang, Y.Z. Huang, J. Chem. Soc., Perkin Trans. I (1995) 95-96.
Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I2 interface modification engineering on the performance of all-inorganic CsPbBr3 perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
Yu Zhou , Lin-Tao Jiang , Xiao-Ming Jiang , Bin-Wen Liu , Guo-Cong Guo . Mixed-anion square-pyramid [SbS3I2] units causing strong second-harmonic generation intensity and large birefringence. Chinese Chemical Letters, 2025, 36(4): 109740-. doi: 10.1016/j.cclet.2024.109740
You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs3Bi2X9 (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
Ya-Wen Zhang , Ming-Ming Gan , Li-Ying Sun , Ying-Feng Han . Supramolecular dinuclear silver(I) and gold(I) tetracarbene metallacycles and fluorescence sensing of penicillamine. Chinese Journal of Structural Chemistry, 2024, 43(9): 100356-100356. doi: 10.1016/j.cjsc.2024.100356
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
Jiaxuan Wang , Tonghe Liu , Bingxiang Wang , Ziwei Li , Yuzhong Niu , Hou Chen , Ying Zhang . Synthesis of polyhydroxyl-capped PAMAM dendrimer/silica composites for the adsorption of aqueous Hg(II) and Ag(I). Chinese Chemical Letters, 2024, 35(12): 109900-. doi: 10.1016/j.cclet.2024.109900
Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)3I3]- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
Liang Ming , Dan Liu , Qiyue Luo , Chaochao Wei , Chen Liu , Ziling Jiang , Zhongkai Wu , Lin Li , Long Zhang , Shijie Cheng , Chuang Yu . Si-doped Li6PS5I with enhanced conductivity enables superior performance for all-solid-state lithium batteries. Chinese Chemical Letters, 2024, 35(10): 109387-. doi: 10.1016/j.cclet.2023.109387
Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
Xinyu Yu , Fei Wu , Xianglang Sun , Linna Zhu , Baoyu Xia , Zhong'an Li . Low-cost dopant-free fluoranthene-based branched hole transporting materials for efficient and stable n-i-p perovskite solar cells. Chinese Chemical Letters, 2024, 35(10): 109821-. doi: 10.1016/j.cclet.2024.109821
Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131