Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp 2 )-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Autor:	Wang Y; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Scrivener SG; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Zuo XD; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Wang R; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Palermo PN; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Murphy E; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Durham AC; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Wang YM; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2021 Sep 22; Vol. 143 (37), pp. 14998-15004. Date of Electronic Publication: 2021 Sep 07.
DOI:	10.1021/jacs.1c07512
Abstrakt:	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.
Databáze:	MEDLINE
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