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

Chromium-Catalyzed Nozaki–Hiyama–Kishi Reaction

Contributor(s):
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.
 

Significance

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.


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Comment

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.


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Review

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


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Publication History

Publication Date:
16 December 2020 (online)

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