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

被引：23

作者：

Wang, Yidong ^{[1
]}

Scrivener, Sarah G. ^{[1
]}

Zuo, Xiao-Dong ^{[1
]}

Wang, Ruihan ^{[1
]}

Palermo, Philip N. ^{[1
]}

Murphy, Ethan ^{[1
]}

Durham, Austin C. ^{[1
]}

Wang, Yi-Ming ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 37期

基金：

美国国家卫生研究院;

关键词：

C-H FUNCTIONALIZATION; REGIOSELECTIVE INTERMOLECULAR ANNULATION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; 2+2 CYCLOADDITION; REARRANGEMENT; ROUTE; HYDROAMINATION; ALLENAMIDES;

D O I：

10.1021/jacs.1c07512

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：14998 / 15004

页数：7

共 112 条

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