Organolanthanide-catalyzed hydroamination

Sukwon Hong, Tobin Jay Marks*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

937 Scopus citations

Abstract

Organolanthanides are highly efficient catalysts for inter- and intramolecular hydroamination of various C-C unsaturations such as alkenes, alkynes, allenes, and dienes. Attractive features of organolanthanide catalysts include very high turnover frequencies and excellent stereoselectivities, rendering this methodology applicable to concise synthesis of naturally occurring alkaloids and other polycyclic azacycles. The general hydroamination mechanism involves turnover-limiting C-C multiple bond insertion into the Ln-N bond, followed by rapid protonolysis by other amine substrates. Sterically less encumbered ligand designs have been developed to improve reaction rates, and metallocene and non-metallocene chiral lanthanide complexes have been synthesized for enantioselective hydroamination.

Original languageEnglish (US)
Pages (from-to)673-686
Number of pages14
JournalAccounts of Chemical Research
Volume37
Issue number9
DOIs
StatePublished - Sep 1 2004

ASJC Scopus subject areas

  • Chemistry(all)

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