Access the full text.
Sign up today, get DeepDyve free for 14 days.
A. Balaban, D. Oniciu, A. Katritzky (2004)
15137807Chem. Rev., 104
M. Arrowsmith, M. Hill, T. Hadlington, G. Kociok-Köhn, C. Weetman, H. Braunschweig, M. Colling, C. Hu, A. Dudnik, V. Weidner, A. Motta, M. Delferro, T. Marks, C. Entwistle, A. Batsanov, J. Howard, M. Fox, T. Marder, X. Fan, J. Zheng, Z. Li, H. Wang, K. Oshima, T. Ohmura, M. Suginome (2011 2003 2014 2004 2015 2012)
12588122 25411889 25846625 22320932Organometallics Inorg. Chem. Nat. Chem. Chem. Commun. J. Am. Chem. Soc. J. Am. Chem. Soc., 30 42 6 137 134
F.-G. Fontaine, D. Stephan, D. Stephan, D. Stephan, G. Erker, D. Stephan, F.-G. Fontaine, M.-A. Courtemanche, M.-A. Légaré, É. Rochette, F.-G. Fontaine, É. Rochette (2017 2016 2015 2015 2013 2017 2018)
26214241 29308653Philos. Trans. R. Soc., A Science Angew. Chem., Int. Ed. J. Am. Chem. Soc. Frustrated Lewis Pairs I and II Coord. Chem. Rev. Acc. Chem. Res., 354 54 137 334 51
M.-A. Légaré, M.-A. Courtemanche, É. Rochette, F.-G. Fontaine (2015)
26228143Science, 349
D. Leonori, V. Aggarwal, C.-Y. Wang, J. Derosa, M. Biscoe, S. Matthew, B. Glasspoole, P. Eisenberger, C. Crudden, D. Imao, B. Glasspoole, V. Laberge, C. Crudden, Y. Lou, P. Cao, T. Jia, Y. Zhang, M. Wang, J. Liao, D. Sandrock, L. Jean-Gérard, C.-y. Chen, S. Dreher, G. Molander, G. Molander, S. Wisniewski, J. Lee, R. McDonald, D. Hall, T. Ohmura, T. Awano, M. Suginome, T. Awano, T. Ohmura, M. Suginome, S. Dreher, P. Dormer, D. Sandrock, G. Molander, X. Feng, H. Jeon, J. Yun, L. Li, S. Zhao, A. Joshi-Pangu, M. Diane, M. Biscoe (2015 2015 2014 2009 2015 2010 2012 2011 2010 2011 2008 2013 2014)
26388985 24684649 19301820 21077687 23025482 22024887 20822146 22129167 18582050 25226092Angew. Chem., Int. Ed. Chem. Sci. J. Am. Chem. Soc. J. Am. Chem. Soc. Angew. Chem., Int. Ed. J. Am. Chem. Soc. J. Am. Chem. Soc. Nat. Chem. J. Am. Chem. Soc. J. Am. Chem. Soc. J. Am. Chem. Soc. Angew. Chem., Int. Ed. J. Am. Chem. Soc., 54 6 136 131 54 132 134 3 132 133 130 52 136
J. Kanth, M. Periasamy, H. Brown, Q. Yin, S. Kemper, H. Klare, M. Oestreich (2000 2016)
27447683Org. Process Res. Dev. Chem.–Eur. J., 4 22
C. Chong, R. Kinjo, S. Park, S. Chang, K. Revunova, G. Nikonov, S. Kirchberg, R. Fröhlich, A. Studer, S. Zhang, Y. Han, J. He, Y. Zhang (2015 2017 2015 2009 2018)
25384615 29284261ACS Catal. Angew. Chem., Int. Ed. Dalton Trans. Angew. Chem., Int. Ed. J. Org. Chem., 5 56 44 48 83
M. Odachowski, A. Bonet, S. Essafi, P. Conti-Ramsden, J. Harvey, D. Leonori, V. Aggarwal (2016)
27384259J. Am. Chem. Soc., 138
M. FerreiraE., M. StolzB. (2006)
18040523Tetrahedron Lett., 47
J. Légaré-Lavergne, A. Jayaraman, Castro Misal, É. Rochette, F.-G. Fontaine (2017)
28901757J. Am. Chem. Soc., 139
J.-D. Chai, M. Head-Gordon, J. Tomasi, B. Mennucci, R. Cammi (2008 2005)
18989472 16092826Phys. Chem. Chem. Phys. Chem. Rev., 10 105
Vries De, A. Prokofjevs, E. Vedejs, Grosso Del, J. Carrillo, M. Ingleson, V. Bagutski, Grosso Del, J. Carrillo, I. Cade, M. Helm, J. Lawson, P. Singleton, S. Solomon, T. Marcelli, M. Ingleson, A. Prokofjevs, W. Kampf, E. Vedejs, Grosso Del, P. Singleton, C. Muryn, M. Ingleson (2012 2015 2013 2011 2011)
22519545 23205640Chem. Rev. Chem. Commun. J. Am. Chem. Soc. Angew. Chem., Int. Ed. Angew. Chem., Int. Ed., 112 51 135 50 50
A. Mfuh, V. Nguyen, B. Chhetri, J. Burch, J. Doyle, V. Nesterov, H. Arman, O. Larionov, J. Lawson, R. Melen, Y. Liu, G. Kehr, C. Daniliuc, G. Erker, J. McGough, J. Cid, M. Ingleson, L. Xu, G. Wang, S. Zhang, H. Wang, L. Wang, L. Liu, J. Jiao, P. Li, Q. Yin, Hendrik Klare, M. Oestreich, K. Chernichenko, M. Lindqvist, B. Kótai, M. Nieger, K. Sorochkina, I. Pápai, T. Repo (2016 2017 2017 2017 2017 2017 2016)
27347688 28157303 28449230 28486749 27003334J. Am. Chem. Soc. Inorg. Chem. Chem.–Eur. J. Chem.–Eur. J. Tetrahedron Angew. Chem., Int. Ed. J. Am. Chem. Soc., 138 56 23 23 73 56 138
T. Krygowski, M. Cyrański, A. Pape, K. Kaliappan, E. Kündig (2001 2000)
11710226 11749310Chem. Rev. Chem. Rev., 101 100
While the dearomatization of indoles by carbonboron bond forming reactions is new and quite promising, they are so far mainly metal-catalyzed. Here, we establish the use of metal-free catalysts in promoting such reactions in an atom-efficient way. The in situ generated ambiphilic aminoborane catalyst (1-Pip-2-BH2-C6H4)2 (Pip = piperidyl) promotes borylative dearomatization of various 1-arylsulfonyl indoles with pinacolborane in a syn addition fashion, with H and Bpin groups added respectively to the 2 and 3 positions of indoles. Catalysis proceeds with good to excellent conversion and essentially with complete regio- and diastereoselectivity. From mechanistic insights and DFT computations, we realized and established that prototypical boranes can also catalyze this borylative dearomatization.
Chemical Science – Royal Society of Chemistry
Published: May 17, 2018
Read and print from thousands of top scholarly journals.
Already have an account? Log in
Bookmark this article. You can see your Bookmarks on your DeepDyve Library.
To save an article, log in first, or sign up for a DeepDyve account if you don’t already have one.
Copy and paste the desired citation format or use the link below to download a file formatted for EndNote
Access the full text.
Sign up today, get DeepDyve free for 14 days.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.