Organolanthanide-catalyzed hydroamination

Sukwon Hong, Tobin J. Marks

Research output: Contribution to journalArticle

919 Citations (Scopus)

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
Pages (from-to)673-686
Number of pages14
JournalAccounts of chemical research
Volume37
Issue number9
DOIs
Publication statusPublished - Sep 1 2004

ASJC Scopus subject areas

  • Chemistry(all)

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