B(C6F5)3-Catalyzed Silylation of Unsaturated Hydrocarbons

  • Xiangqing Feng ,
  • Haifeng Du
Expand
  • a CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
    b University of Chinese Academy of Sciences, Beijing 100049

Received date: 2023-06-12

  Revised date: 2023-07-22

  Online published: 2023-08-15

Supported by

National Natural Science Foundation of China(21825108)

Abstract

Organosilicon compounds have been widely applied in synthetic chemistry, medicinal chemistry, polymer chemistry, organic photoelectric materials and other fields due to their unique properties. The silylation of unsaturated compounds represents one of the most important approaches for the synthesis of organosilicon compounds, which has attracted the intensive attention of chemists, and a great success has been achieved. As a unique non-metallic Lewis acid, B(C6F5)3-catalyzed silylation of unsaturated compounds has made a significant progress in recent years. This subject and the corresponding mechanism are demonstrated.

Cite this article

Xiangqing Feng , Haifeng Du . B(C6F5)3-Catalyzed Silylation of Unsaturated Hydrocarbons[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3544 -3557 . DOI: 10.6023/cjoc202306009

References

[1]
(a) Tacke R.; Wannagat U. In Bioactive Organo-Silicon Compounds, Vol. 84, Springer, Berlin, 1979.
[1]
(b) Colvin E. Silicon in Organic Synthesis II, Butterworth, London, 1981, p. 325.
[1]
(c) Ojima I. The Chemistry of Organic Silicon Compounds, Eds.: Patai, S.; Rappoport, Z., Wiley Interscience, New York, 1989, p. 1479.
[1]
(d) Corey J. Y. Chemistry of Organic Silicon Compounds, Eds: Patai, S.; Rappoport, Z., Wiley, Chichester, 1989; Vols. 1 and 2, pp. 1-56.
[1]
(e) Pukhnarevich V. B.; Lukevics E.; Kopylova L. T.; Voronkov M. G. In Perspectives of Hydrosilylation, Ed.: Lukevics, E., Institute of Organic Synthesis, Riga, 1992.
[1]
(f) Brook M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons, New York, 2000.
[2]
(a) Langkopf E.; Schinzer D. Chem. Rev. 1995, 95, 1375.
[2]
(b) Fleming I.; Barbero A.; Walter D. Chem. Rev. 1997, 97, 2063.
[2]
(c) Sieburth S. M.; Nittoli T.; Mutahi A. M.; Guo L. Angew. Chem., Int. Ed. 1998, 37, 812.
[2]
(d) Mortensen M.; Husmann R.; Veri E.; Bolm C. Chem. Soc. Rev. 2009, 38, 1002.
[2]
(e) Min G. K.; Herna?ndez D.; Skrydstrup T. Acc. Chem. Res. 2013, 46, 457.
[2]
(f) Franz A. K.; Wilson S. O. J. Med. Chem. 2013, 56, 388.
[3]
(a) Cheng C.; Hartwig J. F. Chem. Rev. 2015, 115, 8946.
[3]
(b) Du X.; Huang Z. ACS Catal. 2017, 7, 1227.
[3]
(c) Zhang L.-Z. Ph.D. Dissertation, Lanzhou University, Lanzhou, 2017 (in Chinese).
[3]
(张立志, 博士论文, 兰州大学, 兰州, 2017.)
[3]
(d) Yang X. H.; Gao H. W.; Yan J. L.; Shi L. Chin. J. Org. Chem. 2022, 42, 4122 (in Chinese)
[3]
(杨惜晖, 高皓炜, 闫甲乐, 史雷, 有机化学, 2022, 42, 4122.)
[4]
Piers W. E. Adv. Organomet. Chem. 2005, 52, 1.
[5]
(a) Massey A. G.; Park A. J.; Stone F. G. A. Proc. Chem. Soc. 1963, 212.
[5]
(b) Massey A. G.; Park A. J. J. Organomet. Chem. 1964, 2, 245.
[6]
Piers W. E.; Chivers T. Chem. Soc. Rev. 1997, 26, 345.
[7]
Erker G. Dalton Trans. 2005, 1883.
[8]
(a) Piers W. E.; Marwitz A. J. V.; Mercier L. G. Inorg. Chem. 2011, 50, 12252.
[8]
(b) Melen R. L. Chem. Commun. 2014, 50, 1161.
[8]
(c) Oestreich M.; Hermeke J.; Mohr J. Chem. Soc. Rev. 2015, 44, 2202.
[9]
(a) Welch G. C.; San Juan R. R.; Masuda J. D.; Stephan D. W. Science 2006, 314, 1124.
[9]
(b) Stephan D. W. Acc. Chem. Res. 2015, 48, 306.
[9]
(c) Stephan D. W.; Erker G. Angew. Chem., Int. Ed. 2015, 54, 6400.
[9]
(c) Stephan D. W. J. Am. Chem. Soc. 2015, 137, 10018.
[9]
(d) Stephan D. W. Science 2016, 354, aaf7229.
[9]
(e) Wilkins L. C.; Melen R. L. Coord. Chem. Rev. 2016, 324, 123.
[9]
(f) Stephan D. W. J. Am. Chem. Soc. 2021, 143, 20002.
[10]
(a) Marciniec B. G.; Gulinski J.; Urbaniak W.; Kornetka Z. W. In Comprehensive Handbook on Hydrosilylation, Ed.: Marciniec, B. G., Pergamon, Oxford, U. K. 1992.
[10]
(b) Lewis L. N.; Stein J.; Gao Y.; Colborn R. E.; Hutchins G. Platinum Met. Rev. 1997, 41, 66.
[10]
(c) Roy A. K. Adv. Organomet. Chem. 2007, 55, 1.
[10]
(d) Clarson S. J. Silicon 2009, 1, 57.
[11]
Rubin M.; Schwier T.; Gevorgyan V. J. Org. Chem. 2002, 67, 1936.
[12]
Simonneau A.; Oestreich M. Angew. Chem., Int. Ed. 2013, 52, 11905.
[13]
Keess S.; Simonneau A.; Oestreich M. Organometallics 2015, 34, 790.
[14]
Simonneau A.; Oestreich M. Nat. Chem. 2015, 7, 816.
[15]
Gandhamsetty N.; Park J.; Jeong J.; Park S.-W.; Park S.; Chang S. Angew. Chem., Int. Ed. 2015, 54, 6832.
[16]
Kim Y.; Chang S. Angew. Chem., Int. Ed. 2016, 55, 218.
[17]
Kim E.; Park S.; Chang S. Chem. Eur. J. 2018, 24, 5765.
[18]
Ma Y.; Lou S. J.; Luo G.; Luo Y.; Zhan G.; Nishiura M.; Luo Y.; Hou Z. Angew. Chem., Int. Ed. 2018, 57, 15222.
[19]
Curless L. D.; Ingleson M. J. Organometallics 2014, 33, 7241.
[20]
Ma Y.; Wang B.; Zhang L.; Hou Z. J. Am. Chem. Soc. 2016, 138, 3663.
[21]
Gandhamsetty N.; Joung S.; Park S.-W.; Park S.; Chang S. J. Am. Chem. Soc. 2014, 136, 16780.
[22]
Gandhamsetty N.; Park S.; Chang S. J. Am. Chem. Soc. 2015, 137, 15176.
[23]
Curless L. D.; Clark E. R.; Dunsford J. J.; Ingleson M. J. Chem. Commun. 2014, 50, 5270.
[24]
Han Y.; Zhang S.; He J.; Zhang Y. J. Am. Chem. Soc. 2017, 139, 7399.
[25]
Hazra C. K.; Gandhamsetty N.; Park S.; Chang S. Nature Commun. 2016, 7, 13431.
[26]
Ma Y.; Zhang L.; Luo Y.; Nishiura M.; Hou Z. J. Am. Chem. Soc. 2017, 139, 12434.
[27]
Zhang J.; Park S.; Chang S. J. Am. Chem. Soc. 2018, 140, 13209.
[28]
Long P.-W.; He T.; Oestreich M. Org. Lett. 2020, 22, 7383.
[29]
Long P.-W.; Oestreich M. Org. Lett. 2021, 23, 4834.
Outlines

/