Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp²)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

ABSTRACT: 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.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC8458257 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature