SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 6: 1292 - 1318

DOI: https://doi.org/10.6023/cjoc201801003

Reviews

Progress in Activation of Small Molecules Promoted by Frustrated Lewis Pairs

  • Zhang Zhenbei ,
  • Sun Wei ,
  • Cao Zhishan
Expand
  • a College of Chemistry & Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453003;
    b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000;
    c College of Animal Science and Veterinary Medicine, Henan Institute of Science and Technology, Xinxiang 453003

Received date: 2018-01-03

  Revised date: 2018-02-26

  Online published: 2018-03-08

Supported by

Project supported by the National Natural Science Foundation of China (No. 21473226).

Fold

Abstract

Frustrated Lewis pairs (FLPs) chemistry has grown rapidly during the last decade and provided a new strategy for the activation of a variety of small molecules, such as hydrogen, olefins, alkynes, carbon dioxide, tetrahydrofuran and hydrosilane etc. The activations of these molecules have probided a new method in the utility of main group element. The structure and reactivity of FLPs are reviewed and the recent progress in activation of small molecules promoted by frustrated Lewis pairs is introduced.

Key words： frustrated Lewis pairs; B (C6F5)3; metal-free catalysis; organic synthesis

Cite this article

Zhang Zhenbei , Sun Wei , Cao Zhishan . Progress in Activation of Small Molecules Promoted by Frustrated Lewis Pairs[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1292 -1318 . DOI: 10.6023/cjoc201801003

References

[1] Lewis, G. N. Valence and the Structure of Atoms and Molecules, Chemical Catalogue Company, New York, 1923.
[2] Shore, S. G.; Parry, R. W. J.Am.Chem. Soc. 1955, 77, 6084.
[3] Brown, H. C.; Schlesinger, H. I.; Cardon, S. Z. J. Am.Chem.Soc. 1942, 64, 325.
[4] (a) Wittig, G.; Benz, E. Chem.Ber. 1959, 92, 1999.
(b) Tochtermann, W. Angew.Chem., Int.Ed.Engl. 1966, 5, 351.
[5] (a) Bontemps, S.; Bouhadir, G.; Miqueu, K.; Bourissou, D. J.Am.Chem.Soc. 2006, 128, 12056.
(b) Grobe, J.; Lütke-Brochtrup, K.; Krebs, B.; Lage, M.; Niemeyer, H.-H.; Würthwein E.-U. Z.Naturforsch.B 2006, 61, 882.
(c) Hudnall, T. W.; Kim, Y. M.; Bebbington, M. W. P.; Bourissou, D.; Gabba, F. P. J.Am.Chem.Soc. 2008, 130, 10890.
(d) Chiu, C.-B.; Gabba, F. P. Dalton Trans. 2008, 814.
(e) Lin, T.-P.; Gualco, P.; Ladeira, S.; Amgoune, A.; Bourissou, D.; Gabba, F. P. C.R.Chim. 2010, 13, 1168.
(f) Courtemanche, M. A.; Legare, M. A.; Maron, L.; Fontaine, F. G. J.Am. Chem.Soc. 2013, 135, 9326.
[6] Roesler, R.; Piers, W. E.; Parvez, M. J.Organomet. Chem. 2003, 680, 218.
[7] Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
[8] Welch, G. C.; Stephan, D. W. J.Am. Chem.Soc. 2007, 129, 1880.
[9] Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem.Commun. 2007, 5072.
[10] McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew.Chem., Int.Ed. 2007, 46, 4968.
[11] (a) Peng, B.; Nie, Y. China Terminol. 2010, 12, 44(in Chinese). (彭斌, 聂永, 中国科技术语, 2010, 12, 44.)
(b) Liu, Y.; Du, H. Acta Chim.Sinica 2014, 72, 771(in Chinese). (刘勇兵, 杜海峰, 化学学报, 2014, 72, 711.)
[12] (a)Möming, C. M.; Otten, E.; Kehr, G.; Frölich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643.
(b) Peuser, I.;Neu, R. C.; Zhao, X.; Ulrich, M.; Schirmer, B.; Tannert, J. A.; Kehr, G.; Froehlich, R.; Grimme, S.; Erker, G.; Stephan, D. W. Chem.-Eur. J. 2011, 17, 9640.
[13] (a) Cardenas, A. J. P.; Culotta, B. J.; Warren, T. H.; Grimme, S.; Stute, A.; Frölich, R.; Kehr, G.; Erker, G. Angew.Chem., Int.Ed. 2011, 50, 7567.
(b) Neu, R. C.; Otten, E.; Lough, A.; Stephan, D. W. Chem.Sci. 2011, 2, 170.
[14] Sajid, M.; Klose, A.; Birkmann, B.; Liang, L.; Schirmer, B.; Wiegand, T.; Eckert, H.; Lough, A. J.; Fröhlich, R.; Daniliuc, C. G.; Grimme, S.; Stephan, D. W.; Kehr, G.; Erker, G. Chem.Sci. 2013, 4, 213.
[15] Möming, C. M.; Fröel, S.; Kehr, G.; Frölich, R.; Grimme, S.; Erker, G. J.Am.Chem.Soc. 2009, 131, 12280.
[16] Dureen, M. A.; Stephan, D. W. J.Am.Chem.Soc. 2009, 131, 8396.
[17] (a) Erker, G.; Stephan, D. W. Frustrated Lewis Pairs I Uncovering and Understanding, Springer-Verlag, Berlin, Heidelberg, 2013.
(b) Stephan, D. W.; Erker, G. Angew.Chem., Int.Ed. 2010, 49, 46.
(c) Stephan, D. W.; Erker, G. Angew.Chem., Int.Ed. 2015, 54, 6400.
(d) Lu, Z.; Ye, H.; Wang, H. Top. Curr.Chem. 2013, 334, 59.
(e) Wang, H.; Zheng, Y.; Pan, Z.; Fu, H.; Ling, F.; Zhong, W. Chin. J.Org. Chem. 2017, 37, 301(in Chinese). (王辉, 郑亿, 潘振涛, 傅鸿樑, 凌飞, 钟为慧, 有机化学, 2017, 37, 301.)
(f) Stephan, D. W. Acc.Chem.Res. 2015, 48, 306.
(g) Stephan, D. W. Org.Biomol.Chem. 2012, 10, 5740.
[18] Schulz, F.; Sumerin, V.; Heikkinen, S.; Pedersen, B.; Wang, C.; Atsumi, M.; Leskel, M.; Repo, T.; Pyykkö, P.; Petry, W.; Rieger, B. J.Am. Chem.Soc. 2011, 133, 20245.
[19] Zaher, H.; Ashley, A. E.; Irwin, M.; Thompson, A. L.; Gutmann, M. J.; Kramera, T.; O'Hare D. Chem. Commun. 2013, 49, 9755.
[20] Karkamkar, A.; Parab, K.; Camaioni, D. M.; Neiner, D.; Cho, H. M.; Nielsen, T. K.; Autrey, T. Dalton Trans. 2013, 42, 615.
[21] Kim, H. W.; Rhee, Y. M. Chem.-Eur.J. 2009, 15, 13348.
[22] Bako, I.; Stirling, A.; Balint, S.; Papai, I. Dalton Trans. 2012, 41, 9023.
[23] Rocchigiani, L.; Ciancaleoni, G.; Zuccaccia, C.; Macchioni, A. J. Am.Chem.Soc. 2014, 136, 112.
[24] Marwitz, A. J. V.; Dutton, J. L.; Mercier, L. G.; Piers, W. E. J. Am.Chem.Soc. 2011, 133, 10026.
[25] Zhao, X.; Stephan, D. W. J.Am.Chem.Soc. 2011, 133, 12448.
[26] (a) Rokob, T. A.; Hamza, A.; Stirling, A.; Soos, T.; Papai, I. Angew.Chem., Int.Ed. 2008, 47, 2435.
(b) Grimme, S.; Kruse, H.; Goerigk, L.; Erker, G. Angew.Chem., Int. Ed. 2010, 49, 1402.
[27] Schwendemann, S.; Fröhlich, R.; Kehr, G.; Erker, G. Chem.Sci. 2011, 2, 1842.
[28] (a) Axenov, K.; Mömming, C.; Kehr, G.; Fröhlich, R.; Erker, G. Chem.-Eur. J. 2010, 16, 14069.
(b) Spies, P.; Kehr, G.; Bergander, K.; Wibbeling, B.; Fröhlich, R.; Erker, G. Dalton Trans. 2009, 1534.
[29] Wiegand, T.; Eckert, H.; Ekkert, O.; Fröhlich, R.; Kehr, G.; Erker, G.; Grimme, S. J.Am.Chem.Soc. 2012, 134, 4236.
[30] Wang, X.; Kehr, G.; Daniliuc, C. G.; Erker, G. J.Am.Chem. Soc. 2014, 136, 3293.
[31] (a) Rosorius, C.; Daniliuc, C. G.; Fröhlich, R.; Kehr, G.; Erker, G. J.Organomet.Chem. 2013, 744, 149.
(b) Rosorius, C.; Kehr, G.; Fröhlich, R.; Grimme, S., Erker, G. Organometallics 2011, 30, 4211.
[32] (a) Stute, A.; Kehr, G.; Fröhlich, R.; Erker, G. Chem.Commun. 2011, 47, 4288.
(b) Stute, A.; Kehr, G.; Daniliuc, C. G.; Fröhlich, R.; Erker, G. Dalton Trans. 2013, 42, 4487.
[33] Stute, A.; Heletta, L.; Fröhlich, R.; Daniliuc, C. G.; Kehr, G.; Erker, G. Chem.Commun. 2012, 48, 11739.
[34] Geier, S. J.; Stephan, D. W. J.Am.Chem.Soc. 2009, 131, 3476.
[35] Dureen, M. A.; Stephan, D. W. J.Am.Chem.Soc. 2010, 132, 13559.
[36] Xu, B.-H.; Bussmann, K.; Fröhlich, R.; Daniliuc, C. G.; Brandenburg, J. G.; Grimme, S.; Kehr, G.; Erker, G. Organometallics 2013, 32, 6745.
[37] (a) Schwendemann, S.; Oishi, S.; Saito, S.; Fröhlich, R.; Kehr, G.; Erker, G. Chem.-Asian J. 2013, 8, 212.
(b) Lindqvist, M.; Axenov, K.; Nieger, M.; Raeisaenen, M.; Leskela, M.; Repo T. Chem.-Eur.J. 2013, 19, 10412.
[38] Welch, G. C.; Masuda, J. D.; Stephan, D. W. Inorg.Chem. 2006, 45, 478.
[39] Wang, H., Fröhlich, R.; Kehr, G.; Erker, G. Chem.Commun. 2008, 5966.
[40] (a) Oezguen, T.; Ye, K.-Y.; Daniliuc, C. G.; Wibbeling, B.; Liu, L.; Grimme, S.; Kehr, G.; Erker, G. Chem.-Eur.J. 2016, 22, 5988.
(b) Oezguen, T.; Bergander, K.; Liu, L.; Daniliuc, C. G.; Grimme, S.; Kehr, G.; Erker, G. Chem.-Eur.J. 2016, 22, 11958.
[41] Geier, S. J.; Gilbert, T. M.; Stephan, D. W. J.Am.Chem. Soc. 2008, 130, 12632.
[42] Blagg, R. J.; Lawrence, E. J.; Resner, K.; Oganesyan, V. S.; Herrington, T. J.; Ashley, A. E.; Wildgoose, G. G. Dalton Trans. 2016, 45, 6023.
[43] Ramos, A.; Lough, A. J.; Stephan, D. W. Chem.Commun. 2009, 1118.
[44] (a) Liptau, P.; Neumann, M.; Erker, G.; Kehr, G.; Fröhlich, R.; Grimme, S. Organometallics 2004, 23, 21.
(b) Huber, D. P.; Kehr, G.; Bergander, K.; Fröhlich, R.; Erker, G.; Tanino, S.; Ohki, Y.; Tatsumi, K. Organometallics 2008, 27, 5279.
[45] (a) Axenov, K. V.; Kehr, G.; Fröhlich, R.; Erker, G. J.Am. Chem.Soc. 2009, 131, 3454.
(b) Unverhau, K.; Lübbe, G.; Wibbeling, B.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2010, 29, 5320.
[46] (a) Ullrich, M.; Lough, A. J.; Stephan, D. W. J.Am.Chem. Soc. 2009, 131, 52.
(b) Ullrich, M.; Lough, A. J.; Stephan, D. W. Organometallics 2010, 29, 3647.
[47] Xing, J.-Y.; Buffet, J.-C.; Rees, N. H.; Norby, P.; O'Hare, D. Chem. Commun. 2016, 52, 10478.
[48] (a) Chase, P. A.; Stephan, D. W. Angew.Chem., Int. Ed. 2008, 47, 7433.
(b) Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem.Commun. 2010, 46, 4884.
(c) Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem., Int.Ed. 2008, 47, 7428.
[49] Lam, J.; Guenther, B. A. R.; Farrell, J. M.; Eisenberger, P.; Bestvater, B. P.; Newman, P. D.; Melen, R. L.; Crudden, C. M.; Stephan, D. W. Dalton Trans. 2016, 45, 15303.
[50] Tao, X.; Kehr, G.; Wang, X.; Daniliuc, C. G.; Grimme, S.; Erker, G. Chem.-Eur. J. 2016, 22, 9504.
[51] Chase, P. A.; Jurca, T., Stephan, D. W. Chem.Commun. 2008, 1701.
[52] (a) Tussing, S.; Paradies, J. Dalton Trans. 2016, 45, 6124.
(b) Tussing, S.; Kaupmees, K.; Paradies, J. Chem.-Eur.J. 2016, 22, 7422.
[53] Courtemanche, M.-A.; Rochette, E.; Legare, M.-A.; Bi, W.; Fontaine, F.-G. Dalton Trans. 2016, 45, 6129.
[54] Sumerin, V.; Schulz, F.; Nieger, M.; Leskela, M.; Repo, T.; Rieger, B. Angew.Chem., Int.Ed. 2008, 47, 6001.
[55] (a) Lu, Z. P.; Cheng, Z. H.; Chen, Z. X.; Weng, L. H.; Li, Z. H.; Wang, H. D. Angew.Chem., Int.Ed. 2011, 50, 12227.
(b) Yepes, D.; Jaque, P.; Fernandez, I. Chem.-Eur.J. 2016, 22, 18801.
[56] Geier, S. J.; Gille, A. L.; Gilbert, T. M.; Stephan, D. W. Inorg. Chem. 2009, 48, 10466.
[57] Zheng, J.; Lin, Y.-J.; Wang, H. Dalton Trans. 2016, 45, 6088.
[58] (a) Liu, Y.; Du, H. J.Am.Chem.Soc. 2013, 135, 6810.
(b) Liu, Y.; Du, H. J.Am.Chem.Soc. 2013, 135, 12968.
(c) Wei, S.; Du, H. J.Am.Chem.Soc. 2014, 136, 12261.
(d) Wang, W.; Meng, W.; Du, H. Dalton Trans. 2016, 45, 5945.
(e) Wang, W.; Feng, X.; Du, H. Org.Biomol.Chem. 2016, 14, 6683.
(f) Ren, X.; Du, H. J.Am.Chem.Soc. 2016, 138, 810.
(g) Wang, Y. W.; Chen, W. Q.; Lu, Z. P.; Li, Z. H.; Wang, H. D. Angew.Chem., Int.Ed. 2013, 52, 7496.
[59] (a) Stirling, A.; Hamza, A.; Rokob, T. A.; Papai, I. Chem.Commun. 2008, 3148.
(b) Guo, Y.; Li, S. Eur.J.Inorg.Chem. 2008, 2501.
[60] Zhao, X.; Stephan, D. W. Chem.Sci. 2012, 3, 2123.
[61] Voss, T.; Mahdi, T.; Otten, E.; Fröhlich, R.; Kehr, G.; Stephan, D. W.; Erker, G. Organometallics 2012, 31, 2367.
[62] Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem.-Eur. J. 2010, 16, 3005.
[63] Dornan, P. K.; Longobardi, L. E.; Stephan, D. W. Synlett 2014, 1521.
[64] Ullrich, M.; Seto, K. S.-H.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2009, 2335.
[65] (a) Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6594.
(b) Ye, H. Y.; Lu, Z. P.; You, D.; Chen, Z. X.; Li, Z. H.; Wang, H. D. Angew. Chem., Int.Ed. 2012, 51, 12047.
[66] Yu, J.; Kehr, G.; Daniliuc, C. G.; Erker, G. Chem.Commun. 2016, 52, 1393.
[67] Fukazawa, A.; Yamada, H.; Yamaguchi, S. Angew.Chem., Int. Ed. 2008, 47, 5582.
[68] Klose, A.; Kehr, G.; Daniliuc, C. G.; Erker, G. Dalton Trans. 2016, 45, 2023.
[69] Tanur, C. A.; Stephan, D. W. Organometallics 2011, 30, 3652.
[70] Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6422.
[71] Zhao, X.; Lough, A.; Stephan, D. W. Chem.-Eur.J. 2011, 17, 6731.
[72] Zhao, X.; Gilbert, T. M.; Stephan, D. W. Chem.-Eur.J. 2010, 16, 10304.
[73] Wilkins, L. C.; Gunther, B. A. R.; Walther, M.; Lawson, J. R.; Wirth, T.; Melen, R. L. Angew.Chem., Int.Ed. 2016, 55, 11292.
[74] Mahdi, T.; Stephan, D. W. Angew.Chem., Int.Ed. 2013, 52, 12418.
[75] Wittig, G.; Ruckert, A. Liebigs Ann.Chem. 1950, 566, 101.
[76] Breen, T. L.; Stephan, D. W. Inorg.Chem. 1992, 31, 4019.
[77] (a) Avens, L. R.; Barnhart, D. M.; Burns, C. J.; McKee, S. D. Inorg. Chem. 1996, 35, 537.
(b) Campello, M. P. C.; Domingos, A.; Santos, I. J.Organomet.Chem. 1994, 484, 37.
[78] Evans, W. J.; Leman, J. T.; Ziller, J. W.; Khan, S. I. Inorg. Chem. 1996, 35, 4283.
[79] Mommertz, A.; Leo, R.; Massa, W.; Harms, K.; Dehnicke, K. Z.Anorg. Allg.Chem. 1998, 624, 1647.
[80] (a) Breen, T. L.; Stephan, D. W. Inorg. Chem. 1992, 31, 4019.
(b) Guo, Z. Y.; Bradley, P. K.; Jordan, R. F. Organometallics 1992, 11, 2690.
(c) Polamo, M.; Mutikainen, I.; Leskela, M. Acta Crystallogr.C 1997, 53, 1036.
[81] GomezSaso, M.; Mullica, D. F.; Sappenfield, E.; Stone, F. G. A. Polyhedron 1996, 15, 793.
[82] (a) Chivers, T.; Schatte, G. Eur.J.Inorg.Chem. 2003, 3314.
(b) Kunnari, S. M.; Oilunkaniemi, R.; Laitinen, R. S.; Ahlgren, M. J.Chem. Soc., Dalton.Trans. 2001, 3417.
[83] Campbell, J. P.; Gladfelter, W. L. Inorg.Chem. 1997, 36, 4094.
[84] Zhang, Z.; Miao, C.; Xia, C.; Sun, W. Org.Lett. 2016, 18, 1522.
[85] Birkmann, B.; Voss, T.; Geier, S. J.; Ullrich, M.; Kehr, G.; Erker, G.; Stephan, D. W. Organometallics 2010, 29, 5310.
[86] Sgro, M. J.; Dömer, J.; Stephan, D. W. Chem.Commun. 2012, 48, 7253.
[87] Kreitner, C.; Geier, S. J.; Stanlake, L. J. E.; Caputo, C.; Stephan, D. W. Dalton Trans. 2011, 6771.
[88] Morton, J. G. M.; Dureen, M. A.; Stephan, D. W. Chem.Commun. 2010, 46, 8947.
[89] Neu, R. C.; Menard, G.; Stephan, D. W. Dalton Trans. 2012, 41, 9016.
[90] Zhao, X.; Stephan, D. W. Chem.Commun. 2011, 47, 1833.
[91] Ashley, A. E.; Thompson, A. L.; OIHare, D. Angew.Chem., Int.Ed. 2009, 48, 9839.
[92] Berkefeld, A.; Piers, W. E.; Parvez, M. J.Am.Chem. Soc. 2010, 132, 10660.
[93] Takeuchi, K.; Stephan, D. W. Chem.Commun. 2012, 48, 11304.
[94] Dobrovetsky, R.; Stephan, D. W. J.Am.Chem.Soc. 2013, 135, 4974.
[95] Zhang, Z.; Sun, Q.; Xia, C.; Sun, W. Org.Lett. 2016, 18, 6316.
[96] Liu, L.; Vankova, N.; Heine, T. Phys.Chem.Chem. Phys. 2016, 18, 3567.
[97] Menard, G.; Stephan, D. W. J.Am.Chem.Soc. 2010. 132, 1796.
[98] Menard, G.; Stephan, D. W. Angew.Chem., Int.Ed. 2011, 50, 8396.
[99] (a) Ghoussoub, M.; Yadav, S.; Ghuman, K. K.; Ozin, G. A.; Singh, C. V. ACS Catal. 2016, 6, 7109.
(b) Ghuman, K. K.; Hoch, L. B.; Szymanski, P.; Loh, J. Y. Y.; Kherani, N. P.; El-Sayed, M. A.; Ozin, G. A.; Singh, C. V. J.Am.Chem.Soc. 2016, 138, 1206.
(c) Ghuman, K. K.; Hoch, L. B.; Wood, T. E.; Mims, C.; Singh, C. V.; Ozin, G. A. ACS Catal. 2016, 6, 5764.
[100] Sajid, M.; Kehr, G.; Daniliuc, C. G.; Erker, G. Angew.Chem., Int.Ed. 2014, 53, 1118.
[101] Sajid, M.; Elmer, L. M.; Rosorius, C.; Daniliuc, C. G.; Grimme, S.; Kehr, G.; Erker, G. Angew.Chem., Int.Ed. 2013, 52, 2243.
[102] Ye, K.-Y.; Kehr, G.; Daniliuc, C. G.; Liu, L.; Grimme, S.; Erker, G. Angew.Chem., Int.Ed. 2016, 55, 9216.
[103] (a) Oestreich, M.; Hermeke, J.; Mohr, J. Chem.Soc.Rev. 2015, 44, 2202.
(b) Fernandez-Alvarez, F. J.; Aitani, A. M.; Oro, L. A. Catal.Sci. Technol. 2014, 4, 611.
[104] (a) Houghton, A. Y.; Hurmalainen, J.; Mansikkamaki, A.; Piers, W. E.; Tuononen, H. M. Nat.Chem. 2014, 6, 983.
(b) Nikonov, G. I.; Vyboishchikov, S. F.; Shirobokov, O. G. J.Am. Chem.Soc. 2012, 134, 5488.
(c) Mathew, J.; Eguchi, K.; Nakajima, Y.; Sato, K.; Shimada, S.; Choe, Y. K. Eur. J.Org.Chem. 2017, 4922.
[105] Parks, D. J.; Piers, W. E. J.Am.Chem.Soc. 1996, 118, 9440.
[106] (a) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J.Org. Chem. 2000, 65, 3090.
(b) Sakata, K.; Fujimoto, H. J.Org.Chem. 2013, 78, 12505.
(c) Keess, S.; Simonneau, A.; Oestreich, M. Organometallics 2015, 34, 790.
[107] Blackwell, J. M.; Morrison, D. J.; Piers, W. E. Tetrahedron 2002, 58, 8247.
[108] Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org.Chem. 1999, 64, 4887.
[109] (a) Gevorgyan, V.; Rubin, M.; Liu, J.-X.; Yamamoto, Y. J.Org. Chem. 2001, 66, 1672.
(b) Bezier, D.; Park, S.; Brookhart, M. Org.Lett. 2013, 15, 496.
[110] (a) Bajracharya, G. B.; Nogami, T.; Jin, T.; Matsuda, K.; Gevorgyan, V.; Yamamoto, Y. Synthesis 2004, 308.
(b) Nimmagadda, R. D.; McRae, C. Tetrahedron Lett. 2006, 47, 5755.
(c) Tan, M.; Zhang, Y. Tetrahedron Lett. 2009, 50, 4912.
[111] Porwal, D.; Oestreich, M. Synthesis 2017, 49, 4698.
[112] Adduci, L. L.; McLaughlin, M. P.; Bender, T. A.; Becker, J. J.; Gagne, M. R. Angew.Chem., Int.Ed. 2014, 53, 1646.
[113] Berkefeld, A.; Piers, W. E.; Parvez, M. J.Am.Chem. Soc. 2010, 132, 10660.
[114] Chen, J. W.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y. X. J.Am.Chem.Soc. 2016, 138, 5321.
[115] (a) Harrison, D. J.; McDonald, R.; Rosenberg, L. Organometallics 2005, 24, 1398.
(b) Lee, P. T. K.; Skjel, M. K.; Rosenberg, L. Organometallics 2013, 32, 1575.
(c) Saito, K.; Kondo, K.; Akiyama, T. Org.Lett. 2015, 17, 3366-3369
[116] (a) Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921.
(b) Mewald, M.; Oestreich, M. Chem.-Eur.J. 2012, 18, 14079.
(c) Hermeke, J.; Mewald, M.; Oestreich, M. J.Am.Chem.Soc. 2013, 135, 17537.
[117] (a) Rubin, M.; Schwier, T.; Gevorgyan, V. J.Org.Chem. 2002, 67, 1936.
(b) Simonneau A.; Oestreich, M. Angew.Chem., Int.Ed. 2013, 52, 11905.
(c) Lee, P. T. K.; Rosenberg, L. Dalton Trans. 2017, 46, 8818.
(d) Zhang, L. W.; Wen, Z. G.; Borzov, M.; Nie, W. L. Acta Chim.Sinica 2017, 75, 819(in Chinese). (张露文, 温志国, Borzov Maxim, 聂万丽, 化学学报, 2017, 75, 819.)
[118] (a) Gandhamsetty, N.; Jeong, J.; Park, J.; Park, S.; Chang, S. J. Org.Chem. 2015, 80, 7281.
(b) Gandhamsetty, N.; Park, J.; Jeong, J.; Park, S. W.; Park, S.; Chang, S. Angew. Chem., Int.Ed. 2015, 54, 6832.
[119] Han, Y. X.; Zhang, S. T.; He, J. H.; Zhang, Y. T. J.Am. Chem.Soc. 2017, 139, 7399.
[120] Curless, L. D.; Clark, E. R.; Dunsford, J. J.; Ingleson, M. J. Chem. Commun. 2014, 50, 5270.
[121] (a) Ma, Y. H.; Wang, B. L.; Zhang, L.; Hou, Z. M. J.Am. Chem.Soc. 2016, 138, 3663.
(b) Ma, Y. H.; Zhang, L.; Luo, Y.; Nishiura, M.; Hou, Z. M. J.Am. Chem.Soc. 2017, 139, 12434.
[122] Otten, E.; Neu, R. C.; Stephan, D. W. J.Am.Chem. Soc. 2009, 131, 9918.
[123] Wang, T.; Kehr, G.; Liu, L.; Grimme, S.; Daniliuc, C. G.; Erker, G. J. Am.Chem.Soc. 2016, 138, 4302.
[124] Dureen, M. A.; Welch, G. C.; Gilbert, T. M.; Stephan, D. W. Inorg. Chem. 2009, 48, 9910.
[125] Chase, P. A.; Gille, A. L.; Gilbert, T. M.; Stephan, D. W. Dalton Trans. 2009, 7179.
[126] Zhou, Q.; Zhang, L.; Meng, W.; Feng, X.; Yang, J.; Du, H. Org. Lett. 2016, 18, 5189.
[127] Li, S.; Li, G.; Meng, W.; Du, H. J.Am.Chem.Soc. 2016, 138, 12956.
[128] Fan, X. T.; Zheng, J. H.; Li, Z. H.; Wang, H. D. J.Am. Chem.Soc. 2015, 137, 4916.
[129] Zheng, J.; Fan, X.; Zhou, B.; Li, Z. H.; Wang, H. Chem.Commun. 2016, 52, 4655.
[130] Yu, Z.; Li, Y.; Shi, J.; Ma, B.; Liu, L.; Zhang, J. Angew.Chem., Int.Ed. 2016, 55, 14807.
[131] Caputo, C. B.; Stephan, D. W. Organometallics 2012, 31, 27.
[132] Froemel, S.; Daniliuc, C. G.; Bannwarth, C.; Grimme, S.; Bussmann, K.; Kehr, G.; Erker, G. Dalton Trans. 2016, 45, 19230.
[133] Samigullin, K.; Georg, I.; Bolte, M.; Lerner, H.-W.; Wagner, M. Chem.-Eur. J. 2016, 22, 3478.
[134] Fasano, V.; Radcliffe, J. E.; Ingleson, M. J. ACS Catal. 2016, 6, 1793.
[135] Chernichenko, K.; Lindqvist, M.; Kotai, B.; Nieger, M.; Sorochkina, K.; Papai, I.; Repo, T. J.Am.Chem.Soc. 2016, 138, 4860.
[136] Liu, Y. Z.; Fan, X. T.; Li, Z. H.; Wang, H. D. Chem.Commun. 2017, 53, 10890.
[137] Chen, G.-Q.; Kehr, G.; Daniliuc, C. G.; Erker, G. Dalton Trans. 2016, 45, 6820.

Options
Outlines

/

〈 〉