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Synthesis of Functionalized Vinylgermanes through a New Ruthenium‐Catalyzed Coupling Reaction
Author(s) -
Marciniec Bogdan,
Ławicka Hanna,
Majchrzak Mariusz,
Kubicki Maciej,
Kownacki Ireneusz
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500670
Subject(s) - ruthenium , catalysis , alkene , metathesis , reagent , chemistry , olefin fiber , ethylene , combinatorial chemistry , organic synthesis , metal , polymer chemistry , coupling reaction , organic chemistry , polymerization , polymer
Vinyl‐substituted germanes react stereo‐ and regioselectively with olefins in the presence of complexes containing RuH and RuGe bonds with the formation of functionalized vinylgermanes that cannot be synthesized by olefin cross ‐ metathesis procedures. The reaction opens a new catalytic route for preparation of a class of organogermanes that are potent organometallic reagents for organic synthesis because they show very low toxicity and could replace organotin compounds. The mechanism of this new catalytic route was proven to involve an interesting insertion of the vinylgermane into the RuH bond and β‐Ge transfer to the metal with elimination of ethylene and generation of an RuGe bond, followed by insertion of the alkene into the RuGe bond and β‐H transfer to the metal to eliminate the substituted vinylgermane.