Title |
Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl
|
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Published in |
Journal of the American Chemical Society, March 2017
|
DOI | 10.1021/jacs.7b00892 |
Pubmed ID | |
Authors |
Joseph Derosa, Annabelle L. Cantu, Mark N. Boulous, Miriam L. O’Duill, Joshua L. Turnbull, Zhen Liu, Daizy M. De La Torre, Keary M. Engle |
Abstract |
A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as the source of both the Cl(-) and H(+) and is catalyzed by palladium(II) acetate, with loadings as low as 25 ppm. Removable picolinamide and 8-aminoquinoline bidentate directing groups are used to control the regioselectivity of the chloropalladation step and stabilize the resulting vinylpalladium(II) intermediate for subsequent protodepalladation. This method provides access to a broad array of substituted vinyl chlorides in excellent yields and with high regioselectivity. The products from this transformation were successfully derivatized via Stille-coupling to a variety of trisubstituted alkene products. Reaction progress kinetic analysis (RPKA) was performed, shedding light on a possible mechanism for this catalytic process. |
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Demographic breakdown
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Members of the public | 1 | 50% |
Mendeley readers
Geographical breakdown
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Student > Master | 11 | 20% |
Researcher | 5 | 9% |
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Student > Doctoral Student | 2 | 4% |
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Unknown | 10 | 18% |