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Related Experiment Videos

A regioselective Ru-catalyzed alkene-alkyne coupling.

B M Trost1, M Machacek, M J Schnaderbeck

  • 1Department of Chemistry, Stanford University, CA 94305-5080, USA. bmtrost@leland.stanford.edu

Organic Letters
|July 6, 2000
PubMed
Summary

Silylalkynes react with alkenes, forming vinylsilanes with precise regioselectivity. Subsequent protodesilylation enables regioselective addition of terminal alkynes to alkenes, overcoming typical mixture issues.

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Area of Science:

  • Organic Chemistry
  • Organosilicon Chemistry

Background:

  • Terminal alkynes typically yield mixtures in additions.
  • Regioselective synthesis of vinylsilanes is challenging.

Purpose of the Study:

  • To develop a regioselective method for adding terminal alkynes to alkenes.
  • To synthesize geometrically defined vinylsilanes.

Main Methods:

  • Reaction of silylalkynes with terminal alkenes.
  • Utilizing the silyl substituent for regiocontrol.
  • Protodesilylation of the resulting adducts.

Main Results:

  • Complete regioselectivity in the silylalkyne-alkene reaction.
  • Formation of geometrically defined vinylsilanes.

Related Experiment Videos

  • Successful regioselective addition of terminal alkynes to alkenes via protodesilylation.

    • Conclusions:

    • The silyl substituent directs regioselectivity in alkyne-alkene additions.
    • This method provides a route to regioselectively functionalized vinylsilanes.
    • Enables regioselective addition of terminal alkynes to alkenes.