Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.

Published

Journal Article

We describe the development of Pd-PHOX-catalysed enantioselective couplings of internal dienes with malononitrile and other activated C-pronucleophiles. Reactions are dramatically accelerated by the addition of Et3N·HBArF 4 as a Brønsted acid co-catalyst, enabling a suite of products bearing a variety of alkyl substituents at the stereogenic carbon to be prepared. A series of mechanism-oriented experiments reveal key aspects of the catalytic cycle and the importance of the non-coordinating BArF 4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes.

Full Text

Duke Authors

Cited Authors

  • Park, S; Adamson, NJ; Malcolmson, SJ

Published Date

  • May 2019

Published In

Volume / Issue

  • 10 / 19

Start / End Page

  • 5176 - 5182

PubMed ID

  • 31183071

Pubmed Central ID

  • 31183071

Electronic International Standard Serial Number (EISSN)

  • 2041-6539

International Standard Serial Number (ISSN)

  • 2041-6520

Digital Object Identifier (DOI)

  • 10.1039/c9sc00633h

Language

  • eng