LOGIN TO YOUR ACCOUNT

Username
Password
Remember Me
Or use your Academic/Social account:

CREATE AN ACCOUNT

Or use your Academic/Social account:

Congratulations!

You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.

Important!

Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message

CREATE AN ACCOUNT

Name:
Username:
Password:
Verify Password:
E-mail:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
hansmann, Max; Melen, Rebecca; Rudolph, Matthias; Rominger, Frank; Waderpohl, Hubert; Stephan, Doug; Hashmi, Stephen (2015)
Publisher: American Chemical Society
Languages: English
Types: Article
Subjects: QD
Stoichiometric reaction of B(C6F5)3 with 1,6-enynes are shown to proceed via initial cyclopropanation and formal 1,1-carboboration. Depending on the substitution on the alkene moiety, subsequent ring-opening of the cyclopropane affords either cyclopentane or cyclohexane derivatives in which the C6F5 and B(C6F5)2 adopt a 1,4-positioning. Mechanistically this transformation involves π-activation of the alkyne moiety which triggers cyclopropanation, followed by carboboration. Both the cyclopropanation and subsequent ring-opening are shown to be stereospecific. Both cyclopropanation and 1,4-carboborated products were employed as Lewis acid components in frustrated Lewis pair activation of H2 and CO2.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

    • (1) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259−281.
    • (2) Trost, B. M. Science 1991, 254, 1471−1477.
    • (3) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636− 1638.
    • (4) Trost, B. M. Acc. Chem. Res. 1990, 23, 34−42.
    • (5) Trost, B. M.; Krische, M. J. Synlett 1998, 1998, 1−16.
    • (6) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067−2096.
    • (7) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
    • (8) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200−203.
    • (9) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271−2296.
    • (10) Jimeńez-Nuń̃ez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326−3350.
    • (11) Michelet, V.; Toullec, P. Y.; Genet̂, J.-P. Angew. Chem., Int. Ed.
    • (12) Toullec, P.; Michelet, V. In Computational Mechanisms of Au and Pt Catalyzed Reactions; Soriano, E., Marco-Contelles, J., Eds.; Springer: Berlin Heidelberg, 2011; Vol. 302, p 31.
    • (13) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc.
    • (14) Power, P. P. Nature 2010, 463, 171−177.
    • (15) Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W.
    • Science 2006, 314, 1124−1126.
    • (16) Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46− 76.
    • (17) Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2015, 54, 6400−6441.
    • (18) McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 4968−4971.
    • (19) Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396−8397.
    • (20) Melen, R. L.; Hansmann, M. M.; Lough, A. J.; Hashmi, A. S. K.; Stephan, D. W. Chem. - Eur. J. 2013, 19, 11928−11938.
    • (21) Hansmann, M. M.; Melen, R. L.; Rominger, F.; Hashmi, A. S.
    • K.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 777−782.
    • (22) Hansmann, M. M.; Melen, R. L.; Rominger, F.; Hashmi, A. S.
    • K.; Stephan, D. W. Chem. Commun. 2014, 50, 7243−7245.
    • (23) Chen, C.; Harhausen, M.; Liedtke, R.; Bussmann, K.; Fukazawa, A.; Yamaguchi, S.; Petersen, J. L.; Daniliuc, C. G.; Frohlich, R.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2013, 52, 5992−5996.
    • (24) Melen, R. L. Chem. Commun. 2014, 50, 1161−1174.
    • (25) Lee, S. I.; Chatani, N. Chem. Commun. 2009, 371−384.
    • (26) Bour, C.; Gandon, V. Synlett 2015, 26, 1427.
    • (27) Jiang, C. F.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125−133.
    • (28) Chen, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc.
    • (29) Kehr, G.; Erker, G. Chem. Commun. 2012, 48, 1839−1850.
    • (30) Chen, C.; Eweiner, F.; Wibbeling, B.; Fröhlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem. - Asian J.
    • (31) Chen, C.; Voss, T.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett.
    • (32) Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun.
    • (33) Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc.
    • (34) Ekkert, O.; Tuschewitzki, O.; Daniliuc, C. G.; Kehr, G.; Erker, G. Chem. Commun. 2013, 49, 6992−6994.
    • (35) Feldhaus, P.; Kehr, G.; Fröhlich, R.; Daniliuc, C. G.; Erker, G. Z.
    • Naturforsch., B: J. Chem. Sci. 2013, 68, 666−674.
    • (36) Liedtke, R.; Harhausen, M.; Fröhlich, R.; Kehr, G.; Erker, G.
    • Org. Lett. 2012, 14, 1448−1451.
    • (37) Mobus, J.; Bonnin, Q.; Ueda, K.; Fröhlich, R.; Itami, K.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2012, 51, 1954−1957.
    • (38) Tsao, F. A.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2015, 51, 4287−4289.
    • (39) Tsao, F. A.; Stephan, D. W. Dalton Trans. 2015, 44, 71−74.
    • (40) Liedtke, R.; Tenberge, F.; Daniliuc, C. G.; Kehr, G.; Erker, G. J.
    • Org. Chem. 2015, 80, 2240−2248.
    • (41) Ge, F.; Kehr, G.; Daniliuc, C. G.; Erker, G. Organometallics 2015, 34, 229−235.
    • (42) Eller, C.; Kehr, G.; Daniliuc, C. G.; Erker, G. Chem. Commun.
    • (43) Eller, C.; Kehr, G.; Daniliuc, C. G.; Stephan, D. W.; Erker, G.
    • Chem. Commun. 2015, 51, 7226−7229.
    • (44) Cade, I. A.; Ingleson, M. J. Chem. - Eur. J. 2014, 20, 12874− 12880.
    • (45) Devillard, M.; Brousses, R.; Miqueu, K.; Bouhadir, G.; Bourissou, D. Angew. Chem., Int. Ed. 2015, 54, 5722−5726.
    • (46) Melen, R. L.; Wilkins, L. C.; Kariuki, B. M.; Wadepohl, H.; Gade, L. H.; Hashmi, A. S. K.; Stephan, D. W.; Hansmann, M. M.
    • Organometallics 2015, 34, 4127−4137.
    • (47) Feldmann, A.; Iida, A.; Fröhlich, R.; Yamaguchi, S.; Kehr, G.; Erker, G. Organometallics 2012, 31, 2445−2451.
    • (48) Feldmann, A.; Kehr, G.; Daniliuc, C. G.; Muck-Lichtenfeld, C.; Erker, G. Chem. - Eur. J. 2015, 21, 12456−12464.
    • (49) Warner, A. J.; Lawson, J. R.; Fasano, V.; Ingleson, M. J. Angew.
    • Chem., Int. Ed. 2015, 54, 11245.
    • (50) Dorel, R.; Echavarren, A. M. J. Org. Chem. 2015, 80, 7321.
    • (51) Brooner, R. E. M.; Brown, T. J.; Widenhoefer, R. A. Angew.
    • Chem., Int. Ed. 2013, 52, 6259.
    • (52) Fürstner, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030−5033.
    • (53) Nieto-Oberhuber, C.; Loṕez, S.; Jimeńez-Nuń̃ez, E.; Echavarren, A. M. Chem. - Eur. J. 2006, 12, 5916.
    • (54) Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345− 9353.
    • (55) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc.
    • (56) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am.
    • Chem. Soc. 1998, 120, 9104.
    • (57) Chen, J.; Reibenspies, J.; Derecskei-Kovacs, A.; Burgess, K.
    • Chem. Commun. 1999, 2501−2502.
    • (58) Hsee, L. C.; Sardella, D. J. Magn. Reson. Chem. 1990, 28, 688− 692.
    • (59) Hierso, J.-C. Chem. Rev. 2014, 114, 4838−4867.
    • (60) Zhao, X.; Stephan, D. W. J. Am. Chem. Soc. 2011, 133, 12448− 12450.
    • (61) Hill, E. A.; Park, Y.-W. J. Organomet. Chem. 1988, 356, 1−16.
    • (62) Pei, W.; Krauss, I. J. J. Am. Chem. Soc. 2011, 133, 18514−18517.
    • (63) Morton, J. G. M.; Dureen, M. A.; Stephan, D. W. Chem.
    • Commun. 2010, 46, 8947−8949.
    • (64) Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880−1881.
    • (65) Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643−6646.
    • (66) Marco-Martínez, J.; Buñuel, E.; Loṕez-Durań, R.; Caŕdenas, D. J.
    • Chem. - Eur. J. 2011, 17, 2734−2741.
    • (67) Marco-Martínez, J.; Loṕez-Carrillo, V.; Buñuel, E.; Simancas, R.; Caŕdenas, D. J. J. Am. Chem. Soc. 2007, 129, 1874−1875.
    • (68) Pardo-Rodríguez, V.; Marco-Martínez, J.; Buñuel, E.; Caŕdenas, D. J. Org. Lett. 2009, 11, 4548−4551.
    • (69) Chen, C.; Voss, T.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett.
  • No related research data.
  • No similar publications.

Share - Bookmark

Cite this article