Organolanthanide-catalyzed hydroamination

Sukwon Hong, Tobin J Marks

Research output: Contribution to journalArticle

897 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 2004

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Stereoselectivity
Lanthanoid Series Elements
Catalysts
Alkynes
Alkenes
Alkaloids
Reaction rates
Amines
Ligands
Substrates
propadiene
metallocene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Organolanthanide-catalyzed hydroamination. / Hong, Sukwon; Marks, Tobin J.

In: Accounts of Chemical Research, Vol. 37, No. 9, 09.2004, p. 673-686.

Research output: Contribution to journalArticle

Hong, Sukwon ; Marks, Tobin J. / Organolanthanide-catalyzed hydroamination. In: Accounts of Chemical Research. 2004 ; Vol. 37, No. 9. pp. 673-686.
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