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Chromium-Catalyzed Nozaki–Hiyama–Kishi Reaction
Nozaki–Hiyama–Kishi Reactions Catalytic in Chromium.
J. Am. Chem. Soc. 1996;
Key wordschromium catalysis - Nozaki–Hiyama–Kishi reaction - chemoselectivity - diastereoselectivity
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.
16 December 2020 (online)
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