A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as both the Cl- and H+ source and is catalyzed by palladium(II) acetate. Removable picolinamide and aminoquinoline bidentate directing groups are used to control the regioselectivity of the chloropalladation step and stabilize the resulting vinyl palladium(II) intermediate for subsequent protodepalladation. This method provides access to a broad array of substituted vinyl chlorides in excellent yields and with high regioselectivity.

Palladium(II)-catalyzed directed anti-hydrochlorination of unactivated alkynes with In Situ generated HCl

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.