Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers through Iron-Catalyzed Regioselective C(sp2)–H Functionalization of Allenes

Ruiqi Ding; Yidong Wang; Yi-Ming Wang

doi:10.1055/a-2004-0951

Synthesis, Table of Contents

Synthesis 2023; 55(05): 733-743
DOI: 10.1055/a-2004-0951

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Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers through Iron-Catalyzed Regioselective C(sp²)–H Functionalization of Allenes

Authors

Ruiqi Ding

^aDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
Yidong Wang

^aDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA

^bSchool of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
Yi-Ming Wang ∗

^aDepartment of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA

Abstract

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Abstract

We report a synthesis of allenylic silyl ethers through iron-catalyzed functionalization of the C(sp²)–H bonds of monosubstituted alkylallenes. In the presence of a cyclopentadienyliron dicarbonyl based catalyst and triisopropylsilyl triflate as a silylation agent, a variety of aryl aldehydes were suitable coupling partners in this transformation, furnishing a collection of 1,1-disubstituted allenylic triisopropylsilyl ethers as products in moderate to excellent yields as a single regioisomer. Lithium bistriflimide was identified as a critical additive in this transformation. The optimized protocol was scalable, and the products were amenable to further transformation to give a number of unsaturated, polyfunctional derivatives.

Key words

coupling - Lewis acids - aldehydes - allenes - cyclopentadienyliron complexes - lithium - contrasteric

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References

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