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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1097-1107

http://dx.doi.org/10.1351/pac200880051097

Nickel-catalyzed carbocyanation of alkynes

Yoshiaki Nakao and Tamejiro Hiyama

Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

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  • Ding Lina, Ishida Naoki, Murakami Masahiro, Morokuma Keiji: sp3–sp2 vs sp3–sp3 C–C Site Selectivity in Rh-Catalyzed Ring Opening of Benzocyclobutenol: A DFT Study. J. Am. Chem. Soc. 2014, 136, 169. <http://dx.doi.org/10.1021/ja407422q>
  • Miyazaki Yosuke, Ohta Naoki, Semba Kazuhiko, Nakao Yoshiaki: Intramolecular Aminocyanation of Alkenes by Cooperative Palladium/Boron Catalysis. J. Am. Chem. Soc. 2014, 136, 3732. <http://dx.doi.org/10.1021/ja4122632>
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  • Ishida Naoki, Ikemoto Wataru, Murakami Masahiro: Cleavage of C–C and C–Si σ-Bonds and Their Intramolecular Exchange. J. Am. Chem. Soc. 2014, 140414144645008. <http://dx.doi.org/10.1021/ja502601g>
  • Matsuda Takanori, Sakurai Yusuke: Gold(I)-Catalyzed Ring-Expanding Spiroannulation of Cyclopropenones with Enynes. J. Org. Chem. 2014, 79, 2739. <http://dx.doi.org/10.1021/jo500045n>
  • Ishida Naoki, Sawano Shota, Murakami Masahiro: Stereospecific ring expansion from orthocyclophanes with central chirality to metacyclophanes with planar chirality. Nat Comms 2014, 5. <http://dx.doi.org/10.1038/ncomms4111>
  • Wang Rui, Falck John Russell: Transformations of X (C, O, N)–CN bonds: cases of selective X (C, O, N)–C activation. RSC Adv. 2014, 4, 1062. <http://dx.doi.org/10.1039/c3ra45178j>
  • Minami Yasunori, Yoshiyasu Hirofumi, Nakao Yoshiaki, Hiyama Tamejiro: Highly Chemoselective CarbonCarbon σ-Bond Activation: Nickel/Lewis Acid Catalyzed Polyfluoroarylcyanation of Alkynes. Angew. Chem. 2013, 125, 917. <http://dx.doi.org/10.1002/ange.201207880>
  • Chen Jianming, Zou Gongfeng, Liao Weiwei: Metal-Free Intramolecular Carbocyanation of Activated Alkenes: Functionalized Nitriles Bearing β-Quaternary Carbon Centers. Angew. Chem. 2013, 125, 9466. <http://dx.doi.org/10.1002/ange.201304102>
  • Meng Lingkui, Kamada Yuko, Muto Kei, Yamaguchi Junichiro, Itami Kenichiro: CH Alkenylation of Azoles with Enols and Esters by Nickel Catalysis. Angew. Chem. 2013, 125, 10232. <http://dx.doi.org/10.1002/ange.201304492>
  • Ishida Naoki, Nakanishi Yuuta, Murakami Masahiro: Reactivity Change of Cyclobutanols towards Isocyanates: Rhodium Favors C -Carbamoylation over O -Carbamoylation. Angew. Chem. 2013, 125, 12091. <http://dx.doi.org/10.1002/ange.201306343>
  • Minami Yasunori, Yoshiyasu Hirofumi, Nakao Yoshiaki, Hiyama Tamejiro: Highly Chemoselective CarbonCarbon σ-Bond Activation: Nickel/Lewis Acid Catalyzed Polyfluoroarylcyanation of Alkynes. Angew. Chem. Int. Ed. 2013, 52, 883. <http://dx.doi.org/10.1002/anie.201207880>
  • Chen Jianming, Zou Gongfeng, Liao Weiwei: Metal-Free Intramolecular Carbocyanation of Activated Alkenes: Functionalized Nitriles Bearing β-Quaternary Carbon Centers. Angew. Chem. Int. Ed. 2013, 52, 9296. <http://dx.doi.org/10.1002/anie.201304102>
  • Meng Lingkui, Kamada Yuko, Muto Kei, Yamaguchi Junichiro, Itami Kenichiro: CH Alkenylation of Azoles with Enols and Esters by Nickel Catalysis. Angew. Chem. Int. Ed. 2013, 52, 10048. <http://dx.doi.org/10.1002/anie.201304492>
  • Ishida Naoki, Nakanishi Yuuta, Murakami Masahiro: Reactivity Change of Cyclobutanols towards Isocyanates: Rhodium Favors C -Carbamoylation over O -Carbamoylation. Angew. Chem. Int. Ed. 2013, 52, 11875. <http://dx.doi.org/10.1002/anie.201306343>
  • Enthaler Stephan, Weidauer Maik, Irran Elisabeth, Epping Jan Dirk, Kretschmer Robert, Someya Chika I.: Exploring the reactivity of nickel complexes in hydrodecyanation reactions. Journal of Organometallic Chemistry 2013, 745-746, 262. <http://dx.doi.org/10.1016/j.jorganchem.2013.07.068>
  • Masuda Yusuke, Hasegawa Maki, Yamashita Makoto, Nozaki Kyoko, Ishida Naoki, Murakami Masahiro: Oxidative Addition of a Strained C–C Bond onto Electron-Rich Rhodium(I) at Room Temperature. J. Am. Chem. Soc. 2013, 135, 7142. <http://dx.doi.org/10.1021/ja403461f>
  • Ishida Naoki, Shimamoto Yasuhiro, Yano Takaaki, Murakami Masahiro: 1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams. J. Am. Chem. Soc. 2013, 135, 19103. <http://dx.doi.org/10.1021/ja410910s>
  • Dermenci Alpay, Whittaker Rachel E., Dong Guangbin: Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes. Org. Lett. 2013, 15, 2242. <http://dx.doi.org/10.1021/ol400815y>
  • Okamoto Kazuhiro, Watanabe Masahito, Sakata Naoki, Murai Masahito, Ohe Kouichi: Copper-Catalyzed C–H Cyanation of Terminal Alkynes with Cyanogen Iodide. Org. Lett. 2013, 15, 5810. <http://dx.doi.org/10.1021/ol402863g>
  • Jiang Yuan-Ye, Yu Hai-Zhu, Fu Yao: Mechanistic Study of Borylation of Nitriles Catalyzed by Rh–B and Ir–B Complexes via C–CN Bond Activation. Organometallics 2013, 32, 926. <http://dx.doi.org/10.1021/om301263s>
  • Patra Tuhin, Agasti Soumitra, Akanksha, Maiti Debabrata: Nickel-catalyzed decyanation of inert carbon–cyano bonds. Chem. Commun. 2013, 49, 69. <http://dx.doi.org/10.1039/c2cc36883h>
  • Wang Rui, Falck John R.: Rhodium(i)-catalyzed N–CN bond cleavage: intramolecular β-cyanation of styrenes. Chem. Commun. 2013, 49, 6516. <http://dx.doi.org/10.1039/c3cc43597k>
  • Patra Tuhin, Agasti Soumitra, Modak Atanu, Maiti Debabrata: Nickel-catalyzed hydrogenolysis of unactivated carbon–cyano bonds. Chem. Commun. 2013, 49, 8362. <http://dx.doi.org/10.1039/c3cc44562c>
  • Kumar Puneet, Zhang Kainan, Louie Janis: An Expeditious Route to Eight-Membered Heterocycles By Nickel-Catalyzed Cycloaddition: Low-Temperature C sp 2C sp 3 Bond Cleavage. Angew. Chem. 2012, 124, 8730. <http://dx.doi.org/10.1002/ange.201203521>
  • Kumar Puneet, Zhang Kainan, Louie Janis: An Expeditious Route to Eight-Membered Heterocycles By Nickel-Catalyzed Cycloaddition: Low-Temperature C sp 2C sp 3 Bond Cleavage. Angew. Chem. Int. Ed. 2012, 51, 8602. <http://dx.doi.org/10.1002/anie.201203521>
  • Tobisu Mamoru, Kinuta Hirotaka, Kita Yusuke, Rémond Emmanuelle, Chatani Naoto: Rhodium(I)-Catalyzed Borylation of Nitriles through the Cleavage of Carbon–Cyano Bonds. S J Am Chem Soc 2012, 134, 115. <http://dx.doi.org/10.1021/ja2095975>
  • Koester Dennis C., Kobayashi Masato, Werz Daniel B., Nakao Yoshiaki: Intramolecular Oxycyanation of Alkenes by Cooperative Pd/BPh3 Catalysis. S J Am Chem Soc 2012, 134, 6544. <http://dx.doi.org/10.1021/ja301375c>
  • Ishida Naoki, Sawano Shota, Masuda Yusuke, Murakami Masahiro: Rhodium-Catalyzed Ring Opening of Benzocyclobutenols with Site-Selectivity Complementary to Thermal Ring Opening. J. Am. Chem. Soc. 2012, 134, 17502. <http://dx.doi.org/10.1021/ja309013a>
  • Ishida Naoki, Ikemoto Wataru, Murakami Masahiro: Intramolecular σ-Bond Metathesis Between Carbon–Carbon and Silicon–Silicon Bonds. Org. Lett. 2012, 14, 3230. <http://dx.doi.org/10.1021/ol301280u>
  • Dahy AbdelRahman A., Koga Nobuaki, Nakazawa Hiroshi: Density Functional Theory Study of N–CN and O–CN Bond Cleavage by an Iron Silyl Complex. Organometallics 2012, 31, 3995. <http://dx.doi.org/10.1021/om300232h>
  • Nakao Yoshiaki: Nickel/Lewis Acid-Catalyzed Carbocyanation of Unsaturated Compounds. Bull. Chem. Soc. Jpn. 2012, 85, 731. <http://dx.doi.org/10.1246/bcsj.20120081>
  • Sai Masahiro, Yorimitsu Hideki, Oshima Koichiro: Allyl-, Allenyl-, and Propargyl-Transfer Reactions through Cleavage of CC Bonds Catalyzed by an N-Heterocyclic Carbene/Copper Complex: Synthesis of Multisubstituted Pyrroles. Angew Chem 2011, 123, 3352. <http://dx.doi.org/10.1002/ange.201100631>
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  • Hatakeyama Takuji, Ishizuka Kentaro, Nakamura Masaharu: Cross-Coupling Reactions Catalyzed by Iron Group Metals and N-Heterocyclic Carbenes via Nonconventional Reaction Mechanisms. J Syn Org Chem Jpn 2011, 69, 1282. <http://dx.doi.org/10.5059/yukigoseikyokaishi.69.1282>
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  • Arévalo Alma, García Juventino J.: Bond Activation with Low-Valent Nickel in Homogeneous Systems. Eur J Inorg Chem 2010, 2010, 4063. <http://dx.doi.org/10.1002/ejic.201000621>
  • Nakao Yoshiaki, Yada Akira, Hiyama Tamejiro: Heteroatom-Directed Alkylcyanation of Alkynes. J Am Chem Soc 2010, 132, 10024. <http://dx.doi.org/10.1021/ja1017078>
  • Wang Congyang, Rakshit Souvik, Glorius Frank: Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C−H and C−C Bond Activation. J Am Chem Soc 2010, 132, 14006. <http://dx.doi.org/10.1021/ja106130r>
  • Tobisu Mamoru, Nakamura Ryo, Kita Yusuke, Chatani Naoto: Rhodium-Catalyzed Reductive Decyanation of Nitriles Using Hydrosilane as a Reducing Agent: Scope, Mechanism and Synthetic Application. Bulletin of the Korean Chemical Society 2010, 31, 582. <http://dx.doi.org/10.5012/bkcs.2010.31.03.582>
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  • Hatakeyama Takuji, Hashimoto Sigma, Ishizuka Kentaro, Nakamura Masaharu: Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides. J Am Chem Soc 2009, 131, 11949. <http://dx.doi.org/10.1021/ja9039289>
  • Nakao Yoshiaki, Hiyama Tamejiro: ChemInform Abstract: Nickel-Catalyzed Carbocyanation of Alkynes. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200842267>