NaBH4/I2-Mediated Efficient Iodination of Alcohols
- Corresponding author: Xi Chanjuan, cjxi@tsinghua.edu.cn
Citation:
Fan Zhengning, Zhang Bo, Xi Chanjuan. NaBH4/I2-Mediated Efficient Iodination of Alcohols[J]. Chinese Journal of Organic Chemistry,
;2019, 39(8): 2333-2337.
doi:
10.6023/cjoc201903036
(a) Chambers, R. D.; James, S. R. In Comprehensive Organic Chemistry, Vol. 1, Eds.: Barton, D. H. R.; Ollis, W. D., Pergamon Press, Oxford, 1979, p. 493.
(b) Hudlicky, T. In Chemistry of Functional Groups, Eds.: Patai, S.; Rapport, Z., Wiley, New York, 1983, (Suppl. D), p. 1021.
(c) Bohlmann, R. In Comprehensive Organic Synthesis, Vol. 6, Eds.: Trust, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, p. 203.
(d) Kita, Y.; Matsugi, M. In Radicals in Organic Synthesis, Eds.: Renaud, P.; Sibi, M. P., Wiley-VCH, Weinheim, 2001, p. 1.
(e) Kita, Y.; Gotanda, K.; Sano, A.; Oka, M.; Murata, K.; Suemura, M.; Matsugi, M. Tetrahedron Lett. 1997, 38, 8345.
(f) Kita, Y.; Sano, A.; Yamaguchi, T.; Oka, M.; Gotanda, K.; Matsugi, M. Tetrahedron Lett. 1997, 38, 3549.
(g) Kita, Y.; Sano, A.; Yamaguchi, T.; Oka, M.; Gotanda, K.; Matsugi, M. J. Org. Chem. 1999, 64, 675.
(h) Kita, Y.; Nambu, H.; Ramesh, N. G.; Anilkumar, G.; Matsugi, M. Org. Lett. 2001, 3, 1157.
Villieras, J.; Bacquet, C.; Nonnat, J. F. Bull. Chem. Soc. Fr. 1975, 1997.
(a) Finkelstein, H. A. Ber. Dtsch. Chem. Ges. 1910, 43, 1528.
(b) Willy, W. E.; McKean, D. R.; Garcia, B. A. Bull. Chem. Soc. Jpn. 1976, 49, 1989.
Landini, D.; Albanese, O.; Mottadelli, S.; Penso. M. J. Chem. Soc., Perkin Trans. 1 1992, 2309.
(a) Firouzabadi, H.; Iranpoor, N.; Shaterian, H. Synlett 2000, 65.
(b) Aizpurua, J. M.; Cossio, F. P.; Palomo, C. J. Org. Chem. 1986, 51, 4941.
(c) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Tetrahedron Lett. 2002, 43, 7139.
(d) Liu, Y.; Xu, Y.; Jung, S. H.; Chae, J. Synlett 2012, 2663.
(e) Maloney, D. J.; Hecht, S. M. Org. Lett. 2005, 7, 4297.
Jung, M.E.; Omstein, P. L. Tetrahedron Lett. 1977, 31, 2651.
Fendez, I.; Garcia, B.; Munoz, S.; Pedro, J. R.; Salud, R. Synlett 1993, 489.
(b) Bandgar, B. P.; Bettigeri, S. V. Monatsh. Chem. 2004, 135, 1251.
Martinez, A. G.; Alvarez, R. M.; Vilar, E. T.; Fraile, A. G.; Bamica, J. O.; Hanack, M.; Subramanian, L. R. Tetrahedron Lett. 1987, 28, 6441.
doi: 10.1016/S0040-4039(00)96882-5
Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
doi: 10.1021/jo01322a012
(a) Mandal, A. K.; Mahajan, S. W. Tetrahedron Lett. 1985, 26, 3863.
(b) Vankar, Y. D.; Rao, C. T. Tetrahedron Lett. 1985, 26, 2717.
(a) Larock, R. C. In Comprehensive Organic Transformation, 2nd ed., Wiley VCH, New York, 1999, p. 695.
(b) Iranpoor, N.; Firouzabadi, H.; Jamalian, A.; Kazemi, F. Tetrahedron 2005, 61, 5699.
(c) Iranpoor, N.; Firouzabadi, H.; Gholinejad, M. Can. J. Chem. 2006, 84, 1006.
Reddy, C. K.; Periasamy, M. Tetrahedron Lett. 1989, 30, 5663.
doi: 10.1016/S0040-4039(01)93826-2
Finkielsztein, L. M.; Aguirre, J. M.; Lantano, B.; Alesso, E. N.; Iglesias, G. Y. Synth. Commun. 2004, 34, 895.
doi: 10.1081/SCC-120028362
Combe, S. H.; Hosseini, A.; Song, L-J.; Hausmann, H.; Schreiner, P. R. Org. Lett. 2017, 19, 6156.
doi: 10.1021/acs.orglett.7b03034
Rafiee, M.; Wang, F.; Hruszkewycz, D. P.; Stahl, S. S. J. Am. Chem. Soc. 2018, 140, 22.
doi: 10.1021/jacs.7b09744
Chen, J.; Lin, J.-H.; Xiao, J.-C. Org. Lett. 2018, 20, 3061.
doi: 10.1021/acs.orglett.8b01058
Neuhaus, P.; Henkel, S.; Sander, W. Aust. J. Chem. 2010, 63, 1634.
doi: 10.1071/CH10348
Artaryan, A.; Mardyukov, A.; Kulbitski, K.; Avigdori, I.; Nisnevich, G. A.; Schreiner, P. R.; Gandelman, M. J. Org. Chem. 2017, 82, 7093.
doi: 10.1021/acs.joc.7b00557
Larsen, M. A.; Wilson, C. V.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8633.
doi: 10.1021/jacs.5b04899
Zhu, R.-Y.; He, J.; Wang, X.-C.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 13194.
doi: 10.1021/ja508165a
Lee, C.-H.; Lee, S.-M.; Min, B.-H.; Kim, D.-S.; Jun, C.-H. Org. Lett. 2018, 20, 2468.
doi: 10.1021/acs.orglett.8b00831
Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co2B-CoPOx coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
Zongyi Huang , Cheng Guo , Quanxing Zheng , Hongliang Lu , Pengfei Ma , Zhengzhong Fang , Pengfei Sun , Xiaodong Yi , Zhou Chen . Efficient photocatalytic biomass-alcohol conversion with simultaneous hydrogen evolution over ultrathin 2D NiS/Ni-CdS photocatalyst. Chinese Chemical Letters, 2024, 35(7): 109580-. doi: 10.1016/j.cclet.2024.109580
Tsegaye Tadesse Tsega , Jiantao Zai , Chin Wei Lai , Xin-Hao Li , Xuefeng Qian . Earth-abundant CuFeS2 nanocrystals@graphite felt electrode for high performance aqueous polysulfide/iodide redox flow batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100192-100192. doi: 10.1016/j.cjsc.2023.100192
Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
Shengyu Zhao , Qinhao Shi , Wuliang Feng , Yang Liu , Xinxin Yang , Xingli Zou , Xionggang Lu , Yufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606
Xiping Dong , Xuan Wang , Zhixiu Lu , Qinhao Shi , Zhengyi Yang , Xuan Yu , Wuliang Feng , Xingli Zou , Yang Liu , Yufeng Zhao . Construction of Cu-Zn Co-doped layered materials for sodium-ion batteries with high cycle stability. Chinese Chemical Letters, 2024, 35(5): 108605-. doi: 10.1016/j.cclet.2023.108605
Fabrice Nelly Habarugira , Ducheng Yao , Wei Miao , Chengcheng Chu , Zhong Chen , Shun Mao . Synergy of sodium doping and nitrogen defects in carbon nitride for promoted photocatalytic synthesis of hydrogen peroxide. Chinese Chemical Letters, 2024, 35(8): 109886-. doi: 10.1016/j.cclet.2024.109886
Mingxin Song , Lijing Xie , Fangyuan Su , Zonglin Yi , Quangui Guo , Cheng-Meng Chen . New insights into the effect of hard carbons microstructure on the diffusion of sodium ions into closed pores. Chinese Chemical Letters, 2024, 35(6): 109266-. doi: 10.1016/j.cclet.2023.109266
Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
Shengyu Zhao , Xuan Yu , Yufeng Zhao . A water-stable high-voltage P3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109933-. doi: 10.1016/j.cclet.2024.109933
Changyuan Bao , Yunpeng Jiang , Haoyin Zhong , Huaizheng Ren , Junhui Wang , Binbin Liu , Qi Zhao , Fan Jin , Yan Meng Chong , Jianguo Sun , Fei Wang , Bo Wang , Ximeng Liu , Dianlong Wang , John Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353
Binyang Qin , Mengqi Wang , Shimei Wu , Yining Li , Chilin Liu , Yufei Zhang , Haosen Fan . Carbon dots confined nanosheets assembled NiCo2S4@CDs cross-stacked architecture for enhanced sodium ion storage. Chinese Chemical Letters, 2024, 35(7): 108921-. doi: 10.1016/j.cclet.2023.108921
Fanjun Kong , Yixin Ge , Shi Tao , Zhengqiu Yuan , Chen Lu , Zhida Han , Lianghao Yu , Bin Qian . Engineering and understanding SnS0.5Se0.5@N/S/Se triple-doped carbon nanofibers for enhanced sodium-ion batteries. Chinese Chemical Letters, 2024, 35(4): 108552-. doi: 10.1016/j.cclet.2023.108552
Dongmei Dai , Xiaobing Lai , Xiaojuan Wang , Yunting Yao , Mengmin Jia , Liang Wang , Pengyao Yan , Yaru Qiao , Zhuangzhuang Zhang , Bao Li , Dai-Huo Liu . Increasing (010) active plane of P2-type layered cathodes with hexagonal prism towards improved sodium-storage. Chinese Chemical Letters, 2024, 35(10): 109405-. doi: 10.1016/j.cclet.2023.109405
Jiaojiao Liang , Youming Peng , Zhichao Xu , Yufei Wang , Menglong Liu , Xin Liu , Di Huang , Yuehua Wei , Zengxi Wei . Boron/phosphorus co-doped nitrogen-rich carbon nanofiber with flexible anode for robust sodium-ion battery. Chinese Chemical Letters, 2025, 36(1): 110452-. doi: 10.1016/j.cclet.2024.110452
Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP2/C anode with native oxidation POx component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na3V2(PO4)3 cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643