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Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

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.

SUBMITTER: Li Y

PROVIDER: S-EPMC8162388 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

Li Yangyang Y Li Yuqiang Y Peng Long L Wu Dong D Zhu Lei L Yin Guoyin G

Chemical science 20200909 38

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° car ...[more]

PMID: 34094304

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