Me2Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones

Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 14; pp. 5733 - 5736
Main Authors Cozzi, Pier Giorgio, Rudolph, Jens, Bolm, Carsten, Norrby, Per-Ola, Tomasini, Claudia
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.07.2005
Amer Chemical Soc
Subjects
Chemical reactivity
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
ORGANOZINC REAGENTS
ENANTIOSELECTIVE PHENYLACETYLENE ADDITION
STEREOSELECTIVITY
PROPARGYLIC ALCOHOLS
DIALKYLZINC
TERMINAL ALKYNES
FACILE
ALKYNYLATION
ALKYNYLZINC
PHENYL
Reactivity
Acetylenic compound
Molecular structure
Transition state
Reaction mechanism
Aldehyde
Ketone
Online AccessGet full text

Cover

More Information
Summary:Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave “ligand like”. Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.
Bibliography:ark:/67375/TPS-9WRDMQ42-J
istex:4377AADEB6B7A2CCFAEFBE9FE2D46DF17F957490
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050115r