Ar-BINMOL–Derived Salan–Cu(II) Complex–Catalyzed Silyl-Reformatsky Reaction of Aromatic Aldehydes

Abstract

In this work, we have developed a facile protocol with salan–Cu system for the facile and selective synthesis of β-hydroxyesters via silyl-Reformatsky reaction with α-silylester and aldehydes. The screening and optimization of reaction conditions led to the determination of a practical and efficient procedure in which the salan–Cu exhibited promising catalytic activity in dimethylsulfoxide, in which the silyl-Reformatsky reaction of aromatic aldehydes with α-trimethylsilylmethylacetate gave the corresponding β-hydroxyester derivatives in excellent yields (up to 98%) under fluoride-free reaction conditions.

GRAPHICAL ABSTRACT

Keywords:

• Ar-BINMOL
• aromatic aldehydes
• organosilicon chemistry
• Reformatsky reaction
• salan ligand

ACKNOWLEDGMENTS

X. L. W. thanks F. E. Zhu and C. Q. Sheng for their help.

Notes

^a All reactions were carried out with 5 mol% of catalyst and ligand at room temperature for 48 h.

^b The yield was isolated by flash column.

^c No reaction or only trace product was detected (<5% yield).

^d No addition of salan (1) ligand.

^e No addition of metal salt or other catalyst.

^f The use of 10 mol% of acetic acid.

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