Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Justin S. Marcum, Courtney C. Roberts, Rajith S. Manan, Tia N. Cervarich, Simon J. Meek

Research output: Contribution to journalArticlepeer-review

111 Scopus citations

Abstract

Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

Original languageEnglish (US)
Pages (from-to)15580-15583
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number44
DOIs
StatePublished - Nov 8 2017
Externally publishedYes

Bibliographical note

Funding Information:
Financial support was provided by the NSF (CHE-1665125) and University of North Carolina. C.C.R. is an NSF graduate research fellow. We are grateful to M. Brookhart for helpful discussions and R. Sommer for assistance obtaining the X-ray structure of 19.

Publisher Copyright:
© 2017 American Chemical Society.

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