Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes
Abstract
The cross-electrophile dialkylation of alkenes enables the formation of two C(sp³)–C(sp³) bonds from readily available starting materials in a single transformation, thereby providing a modular and expedient approach to building structural complexity in organic synthesis. Herein, we exploit the disparate electronic and steric properties of alkyl halides with varying degrees of substitution to accomplish their selective activation and addition to alkenes under electrochemical conditions. This method enables regioselective dialkylation of alkenes without the use of a transition-metal catalyst and provides access to a diverse range of synthetically useful compounds.
Copyright and License
© 2023 American Chemical Society.
Acknowledgement
Financial support was provided by NIGMS (R01GM130928; to S.L.) and NSF Center for Synthetic Organic Electrochemistry (CHE-2002158; to K.A.S.). S.L. is grateful to FMC Corporation for a New Investigator Award and the Camille and Henry Dreyfus Foundation for a Camille Dreyfus Teacher-Scholar Award. K.A.S. acknowledges support from the David and Lucile Packard Fellowship for Science. We thank K. R. Meihaus, L. F. T. Novaes, J. I. Martinez Alvarado, and J. Rein for manuscript editing, I. Keresztes and D. Wood for assistance in mass spectrometry data collection and analysis, A. J. Ressler, S. J. Lee, and Z. Lu for assistance in substrate synthesis, and J. Liu for reproducing experiments.
Contributions
L.L. and Y.W. contributed equally.
Conflict of Interest
The authors declare no competing financial interest.
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Additional details
- ISSN
- 1520-5126
- DOI
- 10.1021/jacs.3c06794
- PMCID
- PMC10625357
- National Institutes of Health
- R01GM130928
- National Science Foundation
- CHE-2002158
- FMC (United States)
- Camille and Henry Dreyfus Foundation
- David and Lucile Packard Foundation