Title: Pinacol Boronates by Direct Arene Borylation with Borenium Cations
Abstract: Angewandte Chemie International EditionVolume 50, Issue 9 p. 2102-2106 Communication Pinacol Boronates by Direct Arene Borylation with Borenium Cations† Alessandro Del Grosso, Alessandro Del Grosso Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorPaul J. Singleton, Paul J. Singleton Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorDr. Christopher A. Muryn, Dr. Christopher A. Muryn Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorDr. Michael J. Ingleson, Corresponding Author Dr. Michael J. Ingleson [email protected] Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this author Alessandro Del Grosso, Alessandro Del Grosso Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorPaul J. Singleton, Paul J. Singleton Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorDr. Christopher A. Muryn, Dr. Christopher A. Muryn Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this authorDr. Michael J. Ingleson, Corresponding Author Dr. Michael J. Ingleson [email protected] Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Department of Chemistry, University of Manchester, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4616Search for more papers by this author First published: 05 January 2011 https://doi.org/10.1002/anie.201006196Citations: 179 † This work was supported by the Royal Society (University Research Fellowship to M.J.I.). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Borenium does it direct: A boron analogue of the Friedel–Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme). Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201006196_sm_miscellaneous_information.pdf887.8 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1D. Hall, Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, 2005, and references therein. 2T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508. 3M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164. 4T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271. 5C. Kleeberg, L. Dang, Z. Lin, T. B. Marder, Angew. Chem. 2009, 121, 5454; Angew. Chem. Int. Ed. 2009, 48, 5350. 6S. Claudel, C. Gosmini, J.-M. Paris, J. Perichon, Chem. Commun. 2007, 3667. 7C. Moldoveanu, D. A. Wilson, C. J. Wilson, P. Leowanawat, A.-M. Resemerita, C. Liu, B. M. Rosen, V. Percec, J. Org. 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Publication Year: 2011
Publication Date: 2011-01-05
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 190
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