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The mechanism of the phosphine-free palladium-catalyzed hydroarylation of alkynes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1553-4027
Technical Univeristy of Denmark.
2006 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 39, 12785-12793 p.Article in journal (Refereed) Published
Abstract [en]

The mechanism of the Pd-catalyzed hydroarylation and hydrovinylation reaction of alkynes has been studied by a combination of experimental and theoretical methods (B3LYP), with an emphasis on the phosphine-free version. The regioselectivity of the hydroarylation and hydrovinylation shows unexpected differences, which could be attributed mainly to the higher steric demand of the cyclohexenyl group as compared to the phenyl group. Hydroarylation of alpha,beta-acetylenic carbonyl substrates yields a very unusual anti-Michael selectivity, which is shown to result from reaction of the nonconjugated double bond, leaving the conjugation intact. In all cases were the regioselectivities reproduced by the calculations.

Place, publisher, year, edition, pages
2006. Vol. 128, no 39, 12785-12793 p.
Keyword [en]
Anti Michael selectivity, Hydroarylation, Hydrovinylation, Phosphines
National Category
Theoretical Chemistry
URN: urn:nbn:se:kth:diva-48881DOI: 10.1021/ja061543xISI: 000240795000054OAI: diva2:488417
QC 20120202Available from: 2012-02-01 Created: 2011-11-23 Last updated: 2012-02-02Bibliographically approved

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Ahlquist, MårtenNorrby, Per-Ola
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