Transforming cyclopropanes to enamides via σ-C–C bond eliminative borylation

Shuyu Kang, Jiahang Lv (), Tianhang Wang, Bingcheng Wu, Minyan Wang and Zhuangzhi Shi ()
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Shuyu Kang: Nanjing University
Jiahang Lv: Nanjing University
Tianhang Wang: Nanjing University
Bingcheng Wu: Nanjing University
Minyan Wang: Nanjing University
Zhuangzhi Shi: Nanjing University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Recent strides in C–H borylation have significantly expanded our toolkit for the preparation of organoboronates. Nevertheless, avenues alternative to obtain these compounds via σ-C–C cleavage, thereby facilitating molecular scaffold editing, remain scarce. Several methodologies have been proposed for hydroboration of cyclopropanes by activating C–C bonds, conventionally relying on noble and hazardous metal catalysts to control reaction outcomes. Here, we present a strategy for crafting stereochemically precise γ-borylenamides through ring-opening of cyclopropanes avoiding any metallic entities. Boryl species, generated through a ternary reaction with BCl3, cyclopropanes, and a tertiary amine, selectively undergo C–C bond eliminative borylation under the directing of N-acyl group, thereby ensuring enhanced selectivity and efficiency along the reaction pathway. Such inherently stereoconvergent approach accommodates precursors of diverse geometries, including cis/trans isomeric blends.

Date: 2024
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DOI: 10.1038/s41467-024-51484-6

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