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化学学报 2015

镍催化的芳基硼酸偕二氟炔丙基化反应

DOI: 10.6023/A15010042, PP. 383-387

肖玉兰,潘强,张新刚

Keywords: 镍,芳基硼酸,α,α-二氟炔丙基溴,交叉偶联反应

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Abstract:

偕二氟炔丙基取代的芳烃是一类非常重要的化合物,但传统合成该类化合物的方法却存在很大局限性.以过渡金属催化直接向芳烃偕二氟炔丙基化是一种高效简洁制备上述化合物的方法.以廉价易得的Ni(NO3)2·6H2O为催化剂,首次实现了镍催化下芳基硼酸与α,α-二氟炔丙基溴的偶联反应.该反应不仅温和高效、原料廉价易得、官能团兼容性良好,而且还能进行克量级放大和对生物活性分子的后期氟修饰,从而为新药研发提供了一种有效手段.

References

[1]	For recent reviews, see:(a) Smart, B. E. J. Fluorine Chem.2001, 109, 3.
[2]	(b) Maienfisch, P.; Hall, R. G. Chimia 2004, 58, 93.
[3]	(c) Special issue on “Fluorine in the Life Sciences”, ChemBioChem 2004, 5, 557.
[4]	(d) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[5]	(e) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev.2008, 37, 320.
[6]	Wang, J.; Sanchez-Rosello, M.; Acena, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshok, V. A.; Liu, H. Chem. Rev.2014, 114, 243.
[7]	(a) Gribble, G. W. Chem. Soc. Rev. 1999, 28, 335.
[8]	(b) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
[9]	(c) O'Hagan, D.; Schaffrath, C.; Cobb, S. L.; Hamilton, J. T. G.; Murphy, C. D. Nature 2002, 416, 279.
[10]	(c) Arnaud, C. H. Chem. Eng. News 2014, 92, 34.
[11]	(a) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev.2004, 104, 3079.
[12]	(b) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev.2011, 111, 2937.
[13]	(c) Acetylene Chemistry: Chemistry, Biology and Material Science, Eds.: Diederich, F.; Stang, P. J.; Tykwinski, R. R., Wiley-VCH, Weinheim, 2005.
[14]	(a) Blackburn, C. M.; England, D. A.; Kolkmann, F. J. Chem. Soc. Chem. Commun. 1981, 930.
[15]	(b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 1119.
[16]	(c) Kitazume, T.; Kamazaki, T. Experimental Methods in Organic Fluorine Chemistry, Gordon and Breach Science, Tokyo, 1998.
[17]	(d) Yang, Y.; You, Z.; Qing, F.-L. Acta Chim. Sinica 2012, 70, 2323. (杨义, 游正伟, 卿凤翎, 化学学报, 2012, 70, 2323.)
[18]	For selected reviews, see:(a) Qiu, X.-L.; Xu, X.-H.; Qing, F.-L. Tetrahedron 2010, 66, 789.
[19]	(b) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529.
[20]	(a) Bannwarth, P.; Gree, D.; Gree, R. Tetrahedron Lett. 2010, 51, 2413.
[21]	(b) Khalaf, A.; Gree, D.; Abdallah, H.; Jaber, N.; Hachem, A.; Gree, R. Tetrahedron 2011, 67, 3881.
[22]	(c) Li, Y.; Wheeler, K. A.; Dembinski, R. Org. Biomol. Chem.2012, 10, 2395.
[23]	(d) Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci.USA 2007, 104, 16793.
[24]	(a) Xu, B.; Mashuta, M. S.; Hammond, G. B. Angew. Chem., Int. Ed.2006, 45, 7265.
[25]	(b) Xu, B.; Hammond, G. B. Chem. Eur. J.2008, 14, 10029.
[26]	(c) Mae, M.; Hong, J. A.; Hammond, G. B.; Uneyama, K. Tetrahedron Lett.2005, 46, 1787.
[27]	(d) Surmont, R.; Verniest, G.; Kimpe, N. D. Org. Lett.2009, 11, 2920;
[28]	(e) Lin, J.; Yue, X.; Huang, P.; Cui, D.; Qing, F.-L. Synthesis 2010, 267.
[29]	(a) Kwok, P. -Y.; Muellner, F. W.; Chen, C.-K.; Fried, J. J. Am. Chem. Soc. 1987, 109, 3684.
[30]	(b) Liu, G.; Mori, S.; Wang, X.; Noritake, S.; Tokunaga, E.; Shibata, N. New J. Chem. 2012, 36, 1769;
[31]	(c) Xu, B.; Hammond, G. B. Angew. Chem., Int. Ed. 2005, 44, 7404.
[32]	For palladium catalyzed difluoroalkylation, see:(a) Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed.2014, 53, 1669.
[33]	(b) Min, Q.-Q.; Yin, Z.; Feng, Z.; Guo, W.-H.; Zhang, X. J. Am. Chem. Soc.2014, 136, 1230.
[34]	(c) Xiao, Y.-L.; Zhang, B.; Feng, Z.; Zhang, X. Org. Lett.2014, 16, 4822.
[35]	(d) Yu, Y.-B.; He, G.-Z.; Zhang, X. Angew. Chem., Int. Ed.2014, 53, 10457.
[36]	(e) Gu, J.-W.; Guo, W.-H.; Zhang, X. Org. Chem. Front. 2015, 2, 38.
[37]	(a) Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560.
[38]	(b) Feng, Z.; Chen, F.; Zhang, X. Org. Lett.2012, 14, 1938.
[39]	(c) Feng, Z.; Xiao, Y.-L.; Zhang, X. Org. Chem. Front. 2014, 1, 113.
[40]	Xiao, Y.-L.; Guo, W.-H.; He, G.-Z.; Pan, Q.; Zhang, X. Angew. Chem., Int. Ed.2014, 53, 9909.
[41]	For related radical inhibition experiments studies, see: Huang, X.-T.; Chen, Q.-Y. J. Org. Chem.2001, 66, 4651.
[42]	For mechanistic studies of Ni-catalyzed Suzuki reactions of unactivated alkyl electrophiles, see:(a) Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc.2012, 134, 5794.
[43]	(b) Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc.2013, 135, 624. For early mechanistic studies of Ni-catalyzed Negishi reactions of unactivated alkyl electrophiles, see:
[44]	(c) Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc.2006, 128, 13175.
[45]	(d) Phapale, V. B.; Bunuel, E.; Garcia-Iglesias, M.; Cardenas, D. J. Angew. Chem., Int. Ed.2007, 46, 8790.
[46]	(e) Lin, X.; Phillips, D. L. J. Org. Chem.2008, 73, 3680. For overview of mechanistic issues regarding Ni-catalyzed cross-couplings of unactivated alkyl halides, see:
[47]	(f) Hu, X. Chem. Sci.2011, 2, 1867.

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