Journal article
Characterization of the zwitterionic intermediate in 1,1‐carboboration of alkynes
- Abstract:
- The reaction of a Lewis acidic borane with an alkyne is a key step in a diverse range of main group transformations. Alkyne 1,1‐carboboration, the Wrackmeyer reaction, is an archetypal transformation of this kind. 1,1‐Carboboration has been proposed to proceed through a zwitterionic intermediate. We report the isolation and spectroscopic, structural and computational characterization of the zwitterionic intermediates generated by reaction of B(C6F5)3 with alkynes. The stepwise reactivity of the zwitterion provides new mechanistic insight for 1,1‐carboboration and wider B(C6F5)3 catalysis. Making use of intramolecular stabilization by a ferrocene substituent, we have characterized the zwitterionic intermediate in the solid state and diverted reactivity towards alkyne cyclotrimerization.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, 1.4MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.202003468
Authors
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 59
- Issue:
- 31
- Pages:
- 12731-12735
- Publication date:
- 2020-04-28
- Acceptance date:
- 2020-04-28
- DOI:
- EISSN:
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1521-3773
- ISSN:
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1433-7851
- Language:
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English
- Keywords:
- Pubs id:
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1123243
- Local pid:
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pubs:1123243
- Deposit date:
-
2020-08-02
Terms of use
- Copyright holder:
- Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- Copyright date:
- 2020
- Rights statement:
- © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from Wiley at https://doi.org/10.1002/anie.202003468
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