Amino acid intercalated layered double hydroxide catalyzed chemoselective methylation of phenols and thiophenols with dimethyl carbonate

作者：Subramanian Thirumeni; Dhakshinamoorthy Amarajothi; Pitchumani Kasi^*

来源：Tetrahedron Letters, 2013, 54(52): 7167-7170.

DOI：10.1016/j.tetlet.2013.10.098

• Amino acids
• Layered double hydroxides
• Dimethyl carbonate
• Methylation
• Chemoselectivity
• Green methylating agent

Sixteen different amino acids are intercalated into Mg-Al layered double hydroxides (LDHs) by the reconstruction method and are characterized by powder XRD and FT-IR. The intercalated amino acid-LDHs (AA-LDHs) are used as catalysts for chemoselective O-methylation of phenol and S-methylation of thiophenol with dimethyl carbonate (DMC) as a green methylating agent. The intercalation behavior of various amino acids is influenced by various structural features of amino acids, namely, carbon chain length, structure, and physicochemical properties. In particular, amino acids possessing a hydrophobic side-chain show higher catalytic activity. A suitable reaction mechanism is proposed. The catalyst can also be recycled.

• 出版日期2013-12-25