Regiodivergent synthesis of 1,3- and 1,4-enynes through kinetically favored hydropalladation and ligand-enforced carbopalladation

Pradhan, Tapas R., Kim, Hong Won and Park, Jin Kyoon 2018. Regiodivergent synthesis of 1,3- and 1,4-enynes through kinetically favored hydropalladation and ligand-enforced carbopalladation. Angewandte Chemie International Edition 57 (31) , pp. 9930-9935. 10.1002/anie.201805408

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Abstract

Pd-catalyzed hydroalkynylations were developed that involve ligand-enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o-OMePh)3P and BrettPhos, which allowed the functionalization of various alkynes, including steroids, carbohydrates, alkaloids, chiral ligands, and vitamins. Based on the experimental results, it was proposed that hydro- and carbopalladation processes operated during the formations of the branched and linear products, respectively.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1433-7851
Last Modified:	26 Jan 2024 14:30
URI:	https://orca.cardiff.ac.uk/id/eprint/165583

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