Tris(4-methoxylphenyl)phosphine-Catalyzed C-C Bond Formation Reaction: Mutual Addition of Aromatic Aldehydes and Ethyl Acrylate

Abstract

A highly efficient intermolecular mutual addition of aromatic aldehydes with ethyl acrylate was developed by using tris(4-methoxylphenyl)phosphine as the catalyst. The reaction corresponds to the construction of 1,4-dicarbonyl compound and allylic alcohol fragments, which also provides a new way to form C-C bond.

GRAPHICAL ABSTRACT

Keywords:

• C-C bond formation
• mutual addition
• tris(4-methoxylphenyl)phosphine

ACKNOWLEDGMENT

The authors thank Guangdong Science and Technology Project (No. 2009B020312016) for the financial support of this work.

Notes

^a The reaction was carried out using 0.5 mmol of ethyl acrylate and 0.5 mmol of 1a in solvent (3.0 mL) for the desired reaction time.

^b GC-MS yield.

^a All the reactions were carried out using 0.5 mmol of ethyl acrylate, 0.5 mmol of 1, and 0.2 equiv. of P(p-PhOCH₃)₃ in dioxane (6.0 mL) at 60 °C for the desired reaction time.

^b Isolated yield.