Citation: Li Jianyu, Zeng Jinlong, Chen Jianfeng, Zhao Baoguo. Tris(trimethylsilyl)silane/O₂-Promoted and Photo-accelerated Conversion of Alkyl Iodides to Alcohols[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3853-3857. doi: 10.6023/cjoc202006055 shu

Tris(trimethylsilyl)silane/O₂-Promoted and Photo-accelerated Conversion of Alkyl Iodides to Alcohols

Key Laboratory of Resource Chemistry of Ministry of Education and Shanghai Key Laboratory of Rare Earth Functional Materials, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234

Corresponding author: Chen Jianfeng, jfchen@shnu.edu.cn Zhao Baoguo, zhaobg2006@shnu.edu.cn
Received Date: 26 June 2020
Revised Date: 5 August 2020
Available Online: 18 August 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21672148), the Shanghai Municipal Education Commission (No. 2019-01-07-00-02-E00029) and the Shanghai Engineering Research Center of Green Energy Chemical Engineeringthe National Natural Science Foundation of China 21672148the Shanghai Municipal Education Commission 2019-01-07-00-02-E00029

Figures(2)

A mild method for the conversion of alkyl iodides to alcohols was developed. The transformation was promoted by tris(trimethylsilyl)silane/O₂ and accelerated by photoredox catalysis under visible light irradiation conditions. Various alkyl iodides, including primary, secondary and tertiary iodides, can be smoothly converted to the corresponding alcohols in 38%~99% yields.
- tris(trimethylsilyl)silane,
- photoredox catalysis,
- carbon radical,
- alkyl iodide,
- alcohol
1. [1]
  (a) Larock, R. C. Comprehensive Organic Transformations, 2nd ed., Wiley-VCH, New York, 1999, p. 890.
  (b) Smith, M. D.; March, J. Advanced Organic Chemistry, 6th ed., Wiley-Interscience, New York, 2007, p. 425.
2. [2]
  (a) Harris, M.; Bull, M. J. Synth. Commun. 1985, 15, 1225.
  (b) Alexander, J.; Renyer, M. L.; Veerapanane, H. Synth. Commun. 1995, 25, 3875.
  (c) Ruddick, C. L.; Hodge, P.; Houghton, M. P. Synthesis 1996, 1359.
  (d) Abad, A.; Agulló, C.; Cuñat, A.C.; Navarro, I. Synthesis 2005, 3355.
  (e) Chougala, B. M.; Samundeeswari, S.; Holiyachi, M.; Shastri, L. A. ChemistrySelect 2017, 2, 1290.
  (f) Liu, H.; Liu, J.; Cheng, X.; Jia, X.; Yu, L.; Xu, Q. ChemSusChem 2019, 12, 2994.
3. [3]
  (a) Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980.
  (b) Nakamura, E.; Sato, K.; Imanishi, Y. Synlett 1995, 525.
  (c) Sawamura, M.; Kawaguchi, Y.; Nakamura, E. Synlett 1997, 801.
  (d) Sawamura, M.; Kawaguchi, Y.; Sato, K.; Nakamura, E. Chem. Lett. 1997, 26, 705.
4. [4]
  Cai, Y.-M.; Xu, Y.-T.; Zhang, X.; Gao, W.-X.; Huang, X.-B.; Zhou, Y.-B.; Liu, M.-C.; Wu, H.-Y. Org. Lett. 2019, 21, 8479. doi: 10.1021/acs.orglett.9b03317
5. [5]
  (a) Itoh, A.; Kodama, T.; Inagaki, S.; Masaki, Y. Org. Lett. 2001, 3, 2653.
  (b) Li, J.; Wang, H.; Liu, L.; Sun, J. RSC Adv. 2014, 4, 49974.
  (c) Xu, J.; Liu, N.; Zou, L.; Cheng, F.; Shen, X.; Liu, T.; Lv, H.; Khan, R.; Fan, B. Asian J. Org. Chem. 2019, 8, 261.
6. [6]
  (a) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
  (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
  (c) Dai X.; Xu, X.; Li, X. Chin. J. Org. Chem. 2013, 33, 2046(in Chinese).
  (戴小军, 许孝良, 李小年, 有机化学, 2013, 33, 2046.)
  (d) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
  (e) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
  (f) Matsui, J. K.; Lang, S. B.; Heitz, D. R.; Molander, G. A. ACS Catal. 2017, 7, 2563.
7. [7]
  (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
  (b) Chatgilialoglu, C.; Ferreri, C.; Landais, Y.; Timokhin, V. I. Chem. Rev. 2018, 118, 6516.
8. [8]
  Mills, I. N.; Porras, J. A.; Bernhard, S. Acc. Chem. Res. 2018, 51, 352. doi: 10.1021/acs.accounts.7b00375
9. [9]
  (a) Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A. Jr.; Malliaras, G. G.; Bernhard, S. Chem. Mater. 2005, 17, 5712.
  (b) Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160.
  (c) Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875.
10. [10]
  (a) Stien, D.; Gastaldi, S. J. Org. Chem. 2004, 69, 4464.
  (b) Damont, A.; Médran-Navarrete, V.; Cacheux, F.; Kuhnast, B.; Pottier, G.; Bernards, N.; Marguet, F.; Puech, F.; Boisgard, R.; Dolle, F. J. Med. Chem. 2015, 58, 7449.
  (c) Dudnik, A. S.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 10693.
11. [11]
  (a) Lee, K. C.; Lee, S.-Y.; Choe, Y. S.; Chi, D. Y. Bull. Korean Chem. Soc. 2004, 25, 1225.
  (b) Nicholson, J. S.; Richards, H. C.; Adams, S. S. GB 1030756, 1966.
  (c) Osako, T.; Torii, K.; Hirata, S.; Uozumi, Y. ACS Catal. 2017, 7371.
  (d) Itami, K.; Kamei, T.; Mitsudo, K.; Nokami, T.; Yoshida, J. J. Org. Chem. 2001, 66, 397.
  (e) Khan, S. N.; Zaman, M. K.; Li, R.; Sun, Z. J. Org. Chem. 2020, 85, 5019.
  (f) Sakai, N.; Kawana, K.; Ikeda, R.; Nakaike, Y.; Konakahara, T. Eur. J. Org. Chem. 2011, 2011, 3178.
  (g) Reddy, A. G. K.; Krishna, J.; Satyanarayana, G. ChemistrySelect 2016, 1, 1151.
  (h) Cavedon, C.; Madani, A.; Seeberger, P. H.; Pieber, B. Org. Lett. 2019, 21, 5331.
  (i) Ishibashi, M. J. Polym. Sci. B Polym. Lett. 1964, 2, 789.
  (j) Reddy, M. V.; Kang, S. M.; Yoo, S.; Woo, S. S.; Kim, D. W. RSC. Adv. 2019, 9, 9435.
  (k) Rysak, V.; Descamps-Mandine, A.; Simon, P.; Blanchard, F.; Burylo, L.; Trentesaux, M.; Vandewalle, M.; Collière, V.; Agbossou-Niedercorn, F.; Michon, C. Catal. Sci. Technol. 2018, 8, 3504.
  (l) Green, R. A.; Jolley, K. E.; Al-Hadedi, A. A. M.; Pletcher, D.; Harrowven, D. C.; De Frutos, O.; Mateos, C.; Klauber, D. J.; Rincón, J. A.; Brown, R. C. D. Org. Lett. 2017, 19, 2050.
  (m) Xu, G.; Leloux, S.; Zhang, P.; Meijide Suárez, J.; Zhang, Y.; Derat, E.; Ménand, M.; Bistri-Aslanoff, O.; Roland, S.; Leyssens, T.; Riant, O.; Sollogoub, M. Angew. Chem., Int. Ed. 2020, 59, 7591.
  (n) Ouali, A.; Majoral, J.-P.; Caminade, A.-M.; Taillefer, M. ChemCatChem 2009, 1, 504.
  (o) Rösler, S.; Obenauf, J. Kempe, R. J. Am. Chem. Soc. 2015, 137, 7998.
  (p) Soulard, V.; Villa, G.; Vollmar, D. P.; Renaud, P. J. Am. Chem. Soc. 2018, 140, 155.
  (q) Zhong, R.; Wei, Z.; Zhang, W.; Liu, S.; Liu, Q. Chem 2019, 5, 1552.
  (r) Ungnade, H. E. J. Org. Chem. 1948, 13, 361.
  (s) Weng, W.-Z.; Liang, H.; Zhang, B. Org. Lett. 2018, 20, 4979.
  (t) Polidano, K.; Williams, J. M. J.; Morrill, L. C. ACS Catal. 2019, 9, 8575.
  (u) Tohma, H.; Maegawa, T.; Takizawa, S.; Kita, Y. Adv. Synth. Catal. 2002, 344, 328.
  (v) Parshikov, I. A.; Modyanova, L. V.; Dovgilivich, E. V.; Terent'ev, P. B.; Vorob'eva, L. I.; Grishina, G. V. Chem. Heterocycl. Compd. (Engl. Transl.) 1992, 28, 159.
  (w) Aguilar Troyano, F. J.; Ballaschk, F.; Jaschinski, M.; Ӧzkaya, Y.; Gómez-Suórez, A. Chem. Eur. J. 2019, 25, 14054.
  (x) Bach, R. D.; Taaffee, T. H.; Holubka, J. W. J. Org. Chem. 1980, 45, 3439.
  (y) Boonyarattanakalin, S.; Martin, S. E.; Dykstra, S. A.; Peterson, B. R. J. Am. Chem. Soc. 2004, 126, 16379.
  (z) Matt, C.; Kern, C.; Streuff, J. ACS Catal. 2020, 10. 6409.
  (aa) Pujari, N. S.; Kulkarni, M. R.; Large, M. C. J.; Bassett, I. M.; Ponrathnam, S. J. Appl. Polym. Sci. 2005, 98, 58.
  (ab) Toogood, H. S.; Cheallaigh, A. N.; Tait, S.; Mansell, D. J.; Jervis, A.; Lygidakis, A.; Humphreys, L.; Takano, E.; Gardiner, J. M.; Scrutton, N. S. ACS Synth. Biol. 2015, 4, 1112.
  (ac) Zengin, G. Chem. Nat. Compd. 2011, 47, 550.
1. [1]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
2. [2]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
3. [3]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383
4. [4]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
5. [5]
  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
6. [6]
  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
7. [7]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
8. [8]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
9. [9]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
10. [10]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
11. [11]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
12. [12]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
13. [13]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
14. [14]
  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
15. [15]
  Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
16. [16]
  Minjun Yin , Yuhui Lin , Manli Zhuang , Wei Xiao , Jie Wu . Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide. Chinese Chemical Letters, 2025, 36(3): 109926-. doi: 10.1016/j.cclet.2024.109926
17. [17]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
18. [18]
  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
19. [19]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
20. [20]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(3168)
HTML views(371)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Tris(trimethylsilyl)silane/O2-Promoted and Photo-accelerated Conversion of Alkyl Iodides to Alcohols

Metrics

通讯作者: 陈斌, bchen63@163.com

Tris(trimethylsilyl)silane/O₂-Promoted and Photo-accelerated Conversion of Alkyl Iodides to Alcohols