Literature DB >> 20160853

Platinum(II) Enyne Cycloisomerization Catalysis: Intermediates and Resting States.

D Luke Nelsen1, Michel R Gagné.   

Abstract

In situ generated [(PPP)Pt][BF(4)](2) (PPP = triphos) catalyzes the cycloisomerization of 1,6-enyne-ols by initiative pi-activation of the alkyne. This generates an isolable cationic Pt-alkenyl species which subsequently participates in turnover limiting protonolysis with in situ generated acid. This latter reactivity contrasts cationic Pt-alkyls which are more difficult to protonolyze. Mechanistic studies on isolated Pt-alkenyls, and deuterium labeling helped to elucidate the mechanistic details.

Entities:  

Year:  2009        PMID： 20160853      PMCID： PMC2662608          DOI： 10.1021/om801069s

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  16 in total

1.  Room-temperature Au(I)-catalyzed C-C bond formation through a tandem Friedel-Crafts-type addition/carbocyclization reaction.

Authors:  Patrick Yves Toullec; Emilie Genin; Lucie Leseurre; Jean-Pierre Genêt; Véronique Michelet
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-13       Impact factor: 15.336

2.  Gold(I)-catalyzed asymmetric cycloisomerization of eneallenes into vinylcyclohexenes.

Authors:  Michael A Tarselli; Anthony R Chianese; Stephen J Lee; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Asymmetric oxidative cation/olefin cyclization of polyenes: evidence for reversible cascade cyclization.

Authors:  Charles A Mullen; Alison N Campbell; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Mercuric triflate-catalyzed tandem cyclization leading to polycarbocycles.

Authors:  Hiroshi Imagawa; Tomoaki Iyenaga; Mugio Nishizawa
Journal:  Org Lett       Date:  2005-02-03       Impact factor: 6.005

5.  Au- and pt-catalyzed cycloisomerizations of 1,5-enynes to cyclohexadienes with a broad alkyne scope.

Authors:  Jianwei Sun; Matthew P Conley; Liming Zhang; Sergey A Kozmin
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

6.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 7.  Electrophilic activation of alkenes by platinum(II): so much more than a slow version of palladium(II).

Authors:  Anthony R Chianese; Stephen J Lee; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Reversibility effects on the stereoselectivity of Pt(II)-mediated cascade poly-ene cyclizations.

Authors:  Jeremiah A Feducia; Michel R Gagné
Journal:  J Am Chem Soc       Date:  2007-12-21       Impact factor: 15.419

9.  Pd(II)- and Pt(II)-mediated polycyclization reactions of 1,5- and 1,6-dienes: evidence in support of carbocation intermediates.

Authors:  Jeong Hwan Koh; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

10.  Catalytic carbophilic activation: catalysis by platinum and gold pi acids.

Authors:  Alois Fürstner; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  4 in total

1.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors:  Joseph J Topczewski; John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

2.  Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

Authors:  Gilmar A Brito; Woo-Ok Jung; Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

3.  Gold(I)-catalyzed cascade cyclization of allenyl epoxides.

Authors:  Michael A Tarselli; J Lucas Zuccarello; Stephen J Lee; Michel R Gagné
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

4.  Synthesis of a Novel Type of 2,3'-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles.

Authors:  Lisa Cooper; José Miguel Alonso; Louise Eagling; Helen Newson; Sachini Herath; Christopher Thomson; Andrew Lister; Catherine Howsham; Brian Cox; María Paz Muñoz
Journal:  Chemistry       Date:  2018-03-05       Impact factor: 5.236
  4 in total

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