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The mechanism of the phosphine-free palladium-catalyzed hydroarylation of alkynes
KTH, Skolan för bioteknologi (BIO), Teoretisk kemi och biologi.ORCID-id: 0000-0002-1553-4027
Technical Univeristy of Denmark.
2006 (engelsk)Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, nr 39, s. 12785-12793Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2006. Vol. 128, nr 39, s. 12785-12793
Emneord [en]
Anti Michael selectivity, Hydroarylation, Hydrovinylation, Phosphines
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-48881DOI: 10.1021/ja061543xISI: 000240795000054OAI: oai:DiVA.org:kth-48881DiVA, id: diva2:488417
Merknad
QC 20120202Tilgjengelig fra: 2012-02-01 Laget: 2011-11-23 Sist oppdatert: 2017-12-08bibliografisk kontrollert

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