Synthesis of a constrained ligand comprising carboxylate and amine donor groups via direct 1,8-functionalization of positionally protected fluorene

Add time:07/12/2019    Source:sciencedirect.com

The synthesis of 1,8-bis(dimethylaminomethylethynyl)-3,6-di(tert-butyl)fluorene-9-yl-acetic acid, a potentially dinucleating ligand containing two N-donor and bridging carboxylate groups, is described. The electronically disfavored 1,8-disubstitution of the fluorene ring system was achieved by using tert-butyl protecting groups in the 3- and 6-positions of the fluorene molecule in combination with mercury(II) as a sterically demanding electrophile. The straightforward synthesis of a 1,8-diiodofluorene derivative provides simple general access to 1,8-disubstituted fluorene molecules.

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