Addition reactions to alkynes catalyzed by ruthenium complexes

Makoto Tokunaga, Yasuo Wakatsuki

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Additions to C-C multiple bonds are simple and the most efficient methods in organic synthesis in terms of atom utilization due to avoidance of stoichiometric amounts of by-products. The following catalytic C-C, C-O and C-N bond-constructions by direct additions of nucleophiles to alkynes catalyzed by ruthenium complexes have been developed. 1) Dimerization of terminal alkynes to 1,4-disubstituted butatriens which is an unusual tail-to-tail coupled product. 2) The first example of anti-Markovnikov hydration of terminal alkynes to aldehydes. 3) Intermolecular hydroamination of terminal alkynes with anilines to imines. Some of the reactions proceed in high yields under solvent-free, open-air conditions. Theoretical studies were also performed about transformation of η2-coordinated 1-alkynes to vinylidene complexes which plays important role in regioselectivity of the addition reactions.

Original languageEnglish
Pages (from-to)587-596
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume58
Issue number6
DOIs
Publication statusPublished - Jun 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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