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. 2008;47(48):9334-6.
doi: 10.1002/anie.200802784.

Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature

Sean W Smith  1 , Gregory C Fu
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Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature

Sean W Smith et al. Angew Chem Int Ed Engl. 2008.
No abstract available

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Figures

Scheme 1
Scheme 1
Application of a secondary-secondary Negishi cross-coupling in a formal total synthesis of α-2,7,11-cembranetriene-4,6-diol.
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References

    1. For reviews, see: Frisch AC, Beller M. Angew Chem, Int Ed. 2005;44:674–688.Netherton MR, Fu GC. In: Topics in Organometallic Chemistry: Palladium in Organic Synthesis. Tsuji J, editor. Springer; New York: 2005. pp. 85–108.Netherton MR, Fu GC. Adv Synth Catal. 2004;346:1525–1532.

    1. Ready has reported copper-catalyzed couplings of secondary α-chloroketones with secondary alkylzinc reagents. He postulates that, unlike typical palladium- and nickel-catalyzed cross-couplings, these reactions proceed without oxidative addition of the electrophile to the catalyst. See: Malosh CF, Ready JM. J Am Chem Soc. 2004;126:10240–10241.

    1. For a review of the Negishi reaction, see: Negishi E-i, Hu Q, Huang Z, Wang G, Yin N. In: The Chemistry of Organozinc Compounds. Rappoport Z, Marek I, editors. Wiley; New York: 2006. Chapter 11.

    1. For pioneering studies of nickel-catalyzed Negishi reactions of alkyl electrophiles, see: Devasagayaraj A, Stüdemann T, Knochel P. Angew Chem, Int Ed Engl. 1995;34:2723–2725.Giovannini R, Stüdemann T, Devasagayaraj A, Dussin G, Knochel P. J Org Chem. 1999;64:3544–3553.

    1. For mechanistic studies of nickel-catalyzed Negishi reactions of alkyl electrophiles (including leading references), see: Jones GD, Martin JL, McFarland C, Allen OR, Hall RE, Haley AD, Brandon RJ, Konovalova T, Desrochers PJ, Pulay P, Vicic DA. J Am Chem Soc. 2006;128:13175–13183.. See also: Anderson TJ, Jones GD, Vicic DA. J Am Chem Soc. 2004;126:8100–8101.Lin X, Phillips DL. J Org Chem. 2008;73:3680–3688.

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