Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction

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Abstract

The selective cross-coupling of activated electrophiles with unactivated ones has been regarded as a challenging task in cross-electrophile couplings. Herein we describe a migratory cross-coupling strategy, which can overcome this obstacle to access the desired cross-coupling products. Accordingly, a selective migratory cross-coupling of two alkyl electrophiles has been accomplished by nickel catalysis. Remarkably, this alkyl-alkyl cross-coupling reaction provides a platform to prepare 2°-2° carbon-carbon bonds from 1° and 2° carbon coupling partners. Preliminary mechanistic studies suggest that chain-walking occurs at both alkyl halides in this reaction, thus a catalytic cycle with the key step involving two alkylnickel(ii) species is proposed for this transformation.

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Li, Y., Li, Y., Peng, L., Wu, D., Zhu, L., & Yin, G. (2020). Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction. Chemical Science, 11(38), 10461–10464. https://doi.org/10.1039/d0sc03217d

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