Asymmetric remote functionalisation through metallotropy

Synthetic approaches for the construction of added-value organic molecules are in continuous progress. in spite of key achievements made over the last few decades, most of them keep as common denominator the fact that a reagent or catalyst interacts with the most reactive site of a substrate (= initiation site) where a selective transformation takes place. The initiation and functionalisation sites therefore coincide. Dissociating the initiation site from the functionalisation site often represents a tour de force but may prove to be a powerful synthetic strategy. Breslow has coined the term “remote functionalisation” to define any reactions in which the initial interaction of a reagent/catalyst selectively leads to a transformation at a distant position. As the two sites are structurally distant, a communicative process between them through external or internal induction is needed. The former usually requires a high-molecular weight template that has to be removed once the transformation is achieved while the latter implies the internal migration of the reagent or catalyst along the backbone substrate. The METALATE project has the ambition of breaking up the patterns in the field of remote functionalisation strategies by proposing metallotropy triggered by a dearomatisation/rearomatisation sequence as an appealing internal communicative process between the initiation and functionalisation sites. Although relatively unexplored, such an approach should open up new avenues in asymmetric organic synthesis, providing that the used reagents are both versatile, easily accessible and cheap. This is the reason why we have turned our attention to organometallic ate reagents. More specifically, we will examine the behaviour of such reagents towards aromatic, heteroaromatic, fused polyaromatic and conjugated aromatic derivatives.

Involved researchers:

Dr. Alexandre VASSEUR (Research assistant professor), principal investigator, CNRS

Dr. Philippe GROS (Research director), partner, CNRS

Alexandre PIERRET (PhD student at University of Lorraine), collaborator, CNRS


Partner institution:

French National Centre for Scientific Research (CNRS), centre-east regional office


Administrative contact:

Nathalie PETITJEAN, administrative manager, CNRS

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