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Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C6 F5 )3 -Initiated Grob Fragmentation.


ABSTRACT: Readily available cyclohexa-2,5-dien-1-ylcarbonyl chloride derivatives are introduced as bench-stable HCl surrogates for transfer hydrochlorination of terminal and internal alkenes as well as selected alkynes. The stepwise Grob fragmentation of those acyl chlorides into chloride, carbon monoxide, a low-molecular-weight arene, and a proton is promoted by B(C6 F5 )3 . This decarbonylative transfer process enables the addition of HCl across C-C double and triple bonds with Markovnikov selectivity at room temperature.

SUBMITTER: Xie K 

PROVIDER: S-EPMC9321001 | biostudies-literature |

REPOSITORIES: biostudies-literature

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