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Pure Appl. Chem., 2010, Vol. 82, No. 3, pp. 565-575

http://dx.doi.org/10.1351/PAC-CON-09-11-13

Published online 2010-02-18

Transition-metal-catalyzed cleavage of carbon–selenium bond and addition to alkynes and allenes

Shin-ichi Fujiwara1, Masashi Toyofuku2, Hitoshi Kuniyasu2 and Nobuaki Kambe2*

1 Department of Chemistry, Osaka Dental University, Kuzuha-hanazonocho 8-1, Hirakata Osaka 573-1121, Japan
2 Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan

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  • Soriano Elena, Fernández Israel: Allenes and computational chemistry: from bonding situations to reaction mechanisms. Chem. Soc. Rev. 2014, 43, 3041. <http://dx.doi.org/10.1039/c3cs60457h>
  • Lechel Tilman, Pfrengle Fabian, Reissig Hans-Ulrich, Zimmer Reinhold: Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes. ChemCatChem 2013, 5, 2100. <http://dx.doi.org/10.1002/cctc.201200875>
  • Kuniyasu Hitoshi, Sanagawa Atsushi, Nakane Daisuke, Iwasaki Takanori, Kambe Nobuaki, Bobuatong Karan, Lu Yunpeng, Ehara Masahiro: σ-Bond Metathesis between M–X and RC(O)X′ (M = Pt, Pd; X, X′ = Cl, Br, I): Facile Determination of the Relative ΔG Values of the Oxidative Additions of RC(O)X to an M(0) Complex, Evidence by Density Functional Theory Calculations, and Synthetic Applications. Organometallics 2013, 32, 2026. <http://dx.doi.org/10.1021/om400157a>
  • Sartori Glaubia, Neto José S. S., Pesarico Ana Paula, Back Davi F., Nogueira Cristina W., Zeni Gilson: Bis-vinyl selenides obtained via iron(iii) catalyzed addition of PhSeSePh to alkynes: synthesis and antinociceptive activity. Org. Biomol. Chem. 2013, 11, 1199. <http://dx.doi.org/10.1039/c2ob27064a>
  • Meng Tianhao, Ouyang Kunbing, Xi Zhenfeng: Palladium-catalyzed cleavage of the Me–Si bond in ortho-trimethylsilyl aryltriflates: synthesis of benzosilole derivatives from ortho-trimethylsilyl aryltriflates and alkynes. RSC Adv. 2013, 3, 14273. <http://dx.doi.org/10.1039/c3ra42910e>
  • Fujiwara Shin-ichi, Okuyama Maiko, Tsuda Susumu, Iwasaki Takanori, Kuniyasu Hitoshi, Kambe Nobuaki: Palladium-catalyzed vinylselenation of allenes. Tetrahedron 2012, 68, 10523. <http://dx.doi.org/10.1016/j.tet.2012.10.003>
  • Ozaki Toshiya, Kotani Mao, Kusano Hiroki, Nomoto Akihiro, Ogawa Akiya: Highly regioselective hydroselenation and double-bond isomerization of terminal alkynes with benzeneselenol catalyzed by bis(triphenylphosphine)palladium(II) dichloride. J Organomet Chem 2011, 696, 450. <http://dx.doi.org/10.1016/j.jorganchem.2010.10.005>
  • Liang Yun, Zhang Shaoguang, Xi Zhenfeng: Palladium-Catalyzed Synthesis of Benzosilolo[2,3-b]indoles via Cleavage of a C(sp3)–Si Bond and Consequent Intramolecular C(sp2)–Si Coupling. J Am Chem Soc 2011, 133, 9204. <http://dx.doi.org/10.1021/ja2024959>
  • Panda Snigdha, Krishna G. Rama, Reddy C. Malla, Zade Sanjio S.: Synthesis, characterization and coordination properties of bis(alkyl)selenosalen ligands. Dalton Trans 2011, 40, 6684. <http://dx.doi.org/10.1039/c1dt10114e>
  • Fujiwara Shin-ichi, Toyofuku Masashi, Kuniyasu Hitoshi, Kambe Nobuaki: ChemInform Abstract: Transition Metal Catalyzed Cleavage of Carbon-Selenium Bond and Addition to Alkynes and Allenes. ChemInform 2010, 41, no. <http://dx.doi.org/10.1002/chin.201035237>