What question did this study set out to answer?

To establish an atom-economical catalytic method for synthesizing 1,1-disubstituted alkenes at room temperature using novel ruthenium complexes.

November 17, 2001Journal of the American Chemical Society

Synthesis of 1,1-Disubstituted Alkenes via a Ru-Catalyzed Addition

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To establish an atom-economical catalytic method for synthesizing 1,1-disubstituted alkenes at room temperature using novel ruthenium complexes.
Evaluated two ruthenium catalysts—cyclopentadienylruthenium (triphenylphosphine) camphorsulfonate and cyclopentadienylruthenium tris(acetonitrile) hexafluorophosphate—at ambient temperature in acetone or DMF.
Assessed functional group tolerance across ethers, alcohols, esters, ketones, and amides, and evaluated mechanistic reversibility involving ruthenacyclopentene intermediates.
Catalytic reactions displayed high regioselectivity favoring 1,1-disubstituted over 1,2-disubstituted alkenes, with product ratios ranging from 9:1 to >25:1.
Reactions exhibited high chemoselectivity toward monosubstituted starting alkenes without competition from di- or trisubstituted alkene products, broadly tolerating hydroxyl, silyl ether, PMB ether, ketone, ester, and amide groups.

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Implication

Chemical synthesis study uncovers ruthenium-catalyzed addition of terminal alkynes to alkenes, highlighting an atom-economical route to functionalized 1,1-disubstituted alkenes.

Cite This Study

Trost et al. (2001) studied this question.

synapsesocial.com/papers/6a752fd701b447f0dadc07f4 https://doi.org/10.1021/ja012009m

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Implication

Chemical synthesis study uncovers ruthenium-catalyzed addition of terminal alkynes to alkenes, highlighting an atom-economical route to functionalized 1,1-disubstituted alkenes.

Synthesis of 1,1-Disubstituted Alkenes via a Ru-Catalyzed Addition

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Discussion

Implication

Cite This Study

Synthesis of 1,1-Disubstituted Alkenes via a Ru-Catalyzed Addition

Key Points

Discussion

Implication

Cite This Study

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