Lewis Acid Activation of Carbodicarbene Catalysts for Rh-Catalyzed Hydroarylation of Dienes

Courtney C. Roberts, Desirée M. Matías, Matthew J. Goldfogel, Simon J. Meek

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

The activation of carbodicarbene (CDC)-Rh(I) pincer complexes by secondary binding of metal salts is reported for the catalytic site-selective hydro-heteroarylation of dienes (up to 98% yield and >98:2 γ:α). Reactions are promoted by 5 mol % of a readily available tridentate (CDC)-Rh complex in the presence of an inexpensive lithium salt. The reaction is compatible with a variety of terminal and internal dienes and tolerant of ester, alkyl halide, and boronate ester functional groups. X-ray data and mechanistic experiments provide support for the role of the metal salts on catalyst activation and shed light on the reaction mechanism. The increased efficiency (120 to 22°C) made available by catalytic amounts of metal salts to catalysts containing C(0) donors is a significant aspect of the disclosed studies.

Original languageEnglish (US)
Pages (from-to)6488-6491
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number20
DOIs
StatePublished - May 27 2015
Externally publishedYes

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