RESUMEN
An iron-catalysed C-H functionalisation of simple monosubstituted allenes for the synthesis of 1-tetrahydroisoquinolinyl 1,1-disubstituted allenes is reported. This transformation represents the first example of a direct conversion of allenic C-H bonds to C-C bonds through cross dehydrogenative coupling. The optimized protocol features broad scope and employs mild, functional group tolerant conditions.
RESUMEN
An iron-catalyzed C-H functionalization of simple monosubstituted allenes is reported. An efficient protocol for this process was made possible by the use of a newly developed electron-rich and sterically hindered cationic cyclopentadienyliron dicarbonyl complex as the catalyst and N-sulfonyl hemiaminal ether reagents as precursors to iminium ion electrophiles. Under optimized conditions, the use of a mild, functional-group-tolerant base enabled the conversion of a range of monoalkyl allenes to their allenylic sulfonamido 1,1-disubstituted derivatives, a previously unreported and contrasteric regiochemical outcome for the C-H functionalization of electronically unbiased and directing-group-free allenes.
