Regioselectivity of the C-metalation of 6-furylpurine: importance of directing effects

Inorg Chem. 2015 May 4;54(9):4183-5. doi: 10.1021/acs.inorgchem.5b00450. Epub 2015 Apr 22.

Abstract

We report the C-metalation of 6-furylpurine with Pt(2+), Pd(2+), and Hg(2+). The ligand binds the metal ions in a bidentate fashion, involving the N7 purine atom and one of the furyl carbon atoms. The regioselectivity is determined by the metal ion. Pt(2+) and Pd(2+) coordinate the furyl moiety in its β position and Hg(2+) in its electronically preferred α position.