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Parameterization of Arynophiles: Experimental Investigations Towards a Quantitative Understanding of Aryne Trapping Reactions

Arynes are highly reactive intermediates that may be used strategically in synthesis by trapping with arynophilic reagents. However, “arynophilicity” of such reagents is almost completely anecdotal and predicting which ones will be efficient traps is often challenging. Here, we describe a systematic study to parameterize the arynophilicity of a wide range of reagents known to trap arynes. A relative reactivity scale, based on one-pot competition experiments, is presented by using furan as a reference arynophile and 3-chlorobenzyne as a the aryne. Greater than 15 arynophiles that react in pericyclic reactions, nucleophilic addition, and σ-bond insertion reactions are parameterized with arynophilicity (A) values, and multiple aryne precursors are applicable.