Synfacts 2021; 17(01): 0065
DOI: 10.1055/s-0040-1719244
Metals in Synthesis

Chromium-Catalyzed Nozaki–Hiyama–Kishi Reaction

Mark Lautens
Randy Sanichar
Fürstner A, *, Shi N. Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany
Nozaki–Hiyama–Kishi Reactions Catalytic in Chromium.

J. Am. Chem. Soc. 1996;
118: 12349-12357
DOI: 10.1021/ja9625236.


Fürstner and Shi reported a chromium-catalyzed Nozaki–Hiyama–Kishi reaction that is applicable to a broad substrate scope because it relates to both aldehydes and (pseudo) halides. It employs non-toxic manganese as a stoichiometric reductant to regenerate the active chromium(II) species and affords the products in good to excellent yields.



The authors noted that both CrCl2 and CrCl3 were effective in mediating the reaction. ­Attempts to further improve the catalytic turnover proved successful as the use of either chromocene (Cp2Cr) or CpCrCl2 .THF as pre-catalysts proved successful even at catalytic loadings of ≤1.0 mol% of chromium.



S. Shaw, J. D. White Chem. Rev. 2019, 119, 9381−9426.


Publication History

Publication Date:
16 December 2020 (online)

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