Radical Replacement Process for Ligated Boryl Radical-Mediated Activation of Unactivated Alkyl Chlorides for C(sp3)–C(sp3) Bond Formation
2024

New Method for Activating Unactivated Alkyl Chlorides

publication Evidence: high

Author Information

Author(s): Fang Chang-Zhen, Zhang Bei-Bei, Tu Yong-Liang, Liu Qiang, Wang Zhi-Xiang, Chen Xiang-Yu

Primary Institution: University of Chinese Academy of Sciences

Hypothesis

Can ligated boryl radicals activate unactivated alkyl chlorides to form C(sp3)–C(sp3) bonds?

Conclusion

The study presents a new activation mode for ligated boryl radicals that successfully generates alkyl radicals from unactivated alkyl chlorides.

Supporting Evidence

  • The new method allows for the formation of C(sp3)–C(sp3) bonds using unactivated alkyl chlorides.
  • Radical replacement process was identified as a key mechanism for activating unactivated alkyl chlorides.
  • Various functional groups on unactivated alkyl chlorides were successfully accommodated in the reactions.

Takeaway

Scientists found a way to use special radicals to turn regular alkyl chlorides into useful building blocks for making new chemicals.

Methodology

The study involved mechanistic studies and optimization of reaction conditions to activate unactivated alkyl chlorides using ligated boryl radicals.

Limitations

The method showed limited success with secondary and tertiary alkyl chlorides, yielding only trace amounts of products.

Digital Object Identifier (DOI)

10.1021/jacs.4c10915

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