研究论文

三(三甲硅基)硅烷/氧气促进和可见光加速烷基碘向醇的转化

  • 李健羽 ,
  • 曾金龙 ,
  • 陈剑锋 ,
  • 赵宝国
展开
  • 上海师范大学化学与材料科学学院 资源化学教育部重点实验室和上海市稀土功能材料重点实验室 上海 200234

收稿日期: 2020-06-26

  修回日期: 2020-08-05

  网络出版日期: 2020-08-19

基金资助

国家自然科学基金(No.21672148)、上海市教育委员会(No.2019-01-07-00-02-E00029)和上海市绿色能源化工工程研究中心资助项目.

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

  • Li Jianyu ,
  • Zeng Jinlong ,
  • Chen Jianfeng ,
  • Zhao Baoguo
Expand
  • 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

Received date: 2020-06-26

  Revised date: 2020-08-05

  Online published: 2020-08-19

Supported by

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 Engineering.

摘要

发展了一种由烷基碘向醇转化的温和方法.该反应的发生需要三(三甲硅基)硅烷/氧气存在,同时可以通过可见光照射加速.不同类型的烷基碘化物,如一级、二级和三级烷基碘化物都能顺利发生反应,以38%~99%的收率得到相应的醇化合物.

本文引用格式

李健羽 , 曾金龙 , 陈剑锋 , 赵宝国 . 三(三甲硅基)硅烷/氧气促进和可见光加速烷基碘向醇的转化[J]. 有机化学, 2020 , 40(11) : 3853 -3857 . DOI: 10.6023/cjoc202006055

Abstract

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.

参考文献

[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] (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] (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] 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.
[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] (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] (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] Mills, I. N.; Porras, J. A.; Bernhard, S. Acc. Chem. Res. 2018, 51, 352.
[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] (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] (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.
文章导航

/