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      Recent Advances in Cyanamide Chemistry: Synthesis and Applications

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          Abstract

          The application of alkyl and aryl substituted cyanamides in synthetic chemistry has diversified multi-fold in recent years. In this review, we discuss recent advances (since 2012) in the chemistry of cyanamides and detail their application in cycloaddition chemistry, aminocyanation reactions, as well as electrophilic cyanide-transfer agents and their unique radical and coordination chemistry.

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          Co(III)-catalyzed C-H activation/formal SN-type reactions: selective and efficient cyanation, halogenation, and allylation.

          Da-Gang Yu, Tobias Gensch, Francisco de Azambuja … (2014)
          The first cobalt-catalyzed cyanation, halogenation, and allylation via C-H activation have been realized. These formal SN-type reactions generate valuable (hetero)aryl/alkenyl nitriles, iodides, and bromides as well as allylated indoles using a bench-stable Co(III) catalyst. High regio- and mono-selectivity were achieved for these reactions. Additionally, allylation proceeded efficiently with a turnover number of 2200 at room temperature, which is unprecedented for this Co(III) catalyst. Alkenyl substrates and amides have been successfully utilized in Cp*Co(III)-catalyzed C-H activation for the first time.
          Article 0 comments Cited 120 times – based on 0 reviews     Review now
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            Cobalt-Catalyzed CH Cyanation of Arenes and Heteroarenes

            Jie Li, Lutz Ackermann (2015)
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              Rhodium-Catalyzed Directed C–H Cyanation of Arenes with N-Cyano-N-phenyl-p-toluenesulfonamide

              Tian-Jun Gong, Bin Xiao, Wan-Min Cheng … (2013)
              A Rh-catalyzed directed C-H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this C-H cyanation process, and the reaction tolerates a variety of synthetically important functional groups.
              Article 0 comments Cited 42 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Margaret A. Brimble: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 12 April 2017
                Publication date Collection: April 2017
                Volume: 22
                Issue: 4
                Electronic Location Identifier: 615
                Affiliations
                School of Chemistry, Joseph Banks Laboratories, University of Lincoln, Lincoln LN6 7DL, UK; ranga_prabhath@ 123456yahoo.com (M.R.R.P.); luwilliams@ 123456lincoln.ac.uk (L.W.); shreeshabhat@ 123456yahoo.co.in (S.V.B.)
                Author notes
                [* ]Correspondence: psharma@ 123456lincoln.ac.uk ; Tel.: +44-015-2288-6885
                Article
                Publisher ID: molecules-22-00615
                DOI: 10.3390/molecules22040615
                PMC ID: 6154562
                PubMed ID: 28417938
                SO-VID: a188b6f3-b214-40ea-ae4c-1be4ea8dc871
                Copyright © © 2017 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 09 March 2017
                Date accepted : 07 April 2017
                Categories
                Subject: Review

                Keywords: cyanamide,synthesis,aminocyanation,cycloaddition,electrophilic cyanation,radical reaction,coordination chemistry
                Data availability:
                Keywords: cyanamide, synthesis, aminocyanation, cycloaddition, electrophilic cyanation, radical reaction, coordination chemistry

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