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

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

Publication History

Received: 01 December 2022

Accepted: 26 December 2022

Accepted Manuscript online:
26 December 2022

Article published online:
02 February 2023

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