Addition Reactions to Alkynes Catalyzed by Ruthenium Complexes.

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  • Tokunaga Makoto
    Organometallic Chemistry Laboratory, RIKEN (The Institute of Physical and Chemical Research
  • Wakatsuki Yasuo
    Organometallic Chemistry Laboratory, RIKEN (The Institute of Physical and Chemical Research

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  • ルテニウム触媒によるアルキンヘの付加反応
  • ルテニウム ショクバイ ニ ヨル アルキン エ ノ フカ ハンノウ

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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.

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