Generation of novel nucleophilic organometallic species and their applications to organic synthesis

Kazuhiko Takai, Clayton H. Heathcock

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Development of nucleophilic organometallic species plays an important role in organic synthesis, especially for construction of carbon skeletons. This account describes the following synthetic reactions with novel organometallic species: (1) Preparation of alkenylchromium reagents for chemoselective addition to aldehydes, (2) Generation of geminai dimetallic species of zinc and chromium for the Wittig-type olefination, (3) Preparation of tantalum-alkyne complexes and their synthetic use, (4) Activation and deactivation of zinc with a catalytic amount of lead, (5) Control of one-electron transfer and its application to sequential radical and anionic reactions, (6) Rhenium and manganese catalyzed-Barbier-type addition of aromatic compounds to aldehydes based on C-H bond activation. The account focuses on the background to the research and how the reactions were discovered.

Original languageEnglish
Pages (from-to)3-18
Number of pages16
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume68
Issue number1
DOIs
Publication statusPublished - Jan 2010

Fingerprint

Organometallics
Aldehydes
Zinc
Chemical activation
Tantalum
Rhenium
Alkynes
Aromatic compounds
Chromium
Manganese
Carbon
Electrons
Lead

Keywords

  • Activation of metal
  • C-H bond activation
  • Chemoselective addition
  • Chromium
  • Manganese
  • One-electron transfer
  • Rhenium
  • Tantalum
  • Titanium
  • Wittig-type olefination

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Development of nucleophilic organometallic species plays an important role in organic synthesis, especially for construction of carbon skeletons. This account describes the following synthetic reactions with novel organometallic species: (1) Preparation of alkenylchromium reagents for chemoselective addition to aldehydes, (2) Generation of geminai dimetallic species of zinc and chromium for the Wittig-type olefination, (3) Preparation of tantalum-alkyne complexes and their synthetic use, (4) Activation and deactivation of zinc with a catalytic amount of lead, (5) Control of one-electron transfer and its application to sequential radical and anionic reactions, (6) Rhenium and manganese catalyzed-Barbier-type addition of aromatic compounds to aldehydes based on C-H bond activation. The account focuses on the background to the research and how the reactions were discovered.",
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