Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether

Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully tr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-03, Vol.53 (27), p.3894-3897
Main Authors: Hari Babu, Madala, Ranjith Kumar, Gadi, Kant, Ruchir, Sridhar Reddy, Maddi
Format: Article
Language:English
Subjects:
Alkynes
Amines
Catalysis
Olefins
Selectivity
Switches
Terminals
Tethers
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Summary:Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc10256e