Ring-Opening Reactions of NHC-Boriranes with In Situ Generated HCl: Synthesis of a New Class of NHC-Boralactones.
J Am Chem Soc
; 141(8): 3623-3629, 2019 02 27.
Article
in En
| MEDLINE
| ID: mdl-30717598
ABSTRACT
The first ring-opening reactions of ligated boriranes (boracyclopropanes) are described. Treatment of readily available NHC-boriranes bearing ester substituents on the borirane ring with HCl provides stable γ-NHC-bora-γ-lactones in isolated yields ranging from 40% to 73%. The reactions occur through 1,3-addition of HCl across a B-C bond of the NHC-borirane to form a ring-opened NHC-boryl chloride, followed by lactonization with chloride displacement. Experimental evidence suggests that both the borirane ring-opening reaction and the boralactonization reaction occur with inversion at boron.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Am Chem Soc
Year:
2019
Document type:
Article
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