Development of the “Diverted Heck” Reaction for the Synthesis of Five-Membered Rings

The “diverted Heck” reaction has been shown to be a potent method to synthesize cyclopropanes from electron-rich olefins and iodomethyl trifluoroborate. Nevertheless, it is not mechanistically limited to the three-membered rings. The synthesis of five-membered rings using bifunctional substrates wit...

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Bibliographic Details
Published in:Organometallics 2021-03, Vol.40 (6), p.776-782
Main Authors: Breitwieser, Kevin, Chen, Peter
Format: Article
Language:English
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Summary:The “diverted Heck” reaction has been shown to be a potent method to synthesize cyclopropanes from electron-rich olefins and iodomethyl trifluoroborate. Nevertheless, it is not mechanistically limited to the three-membered rings. The synthesis of five-membered rings using bifunctional substrates with a halide moiety and an organometallic group is described. Furthermore, the reactions of the respective boron and tin-based substrates are further investigated and optimized.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.1c00025