Formation of a peri-Bridged Phosphonio-Naphthalene by Cu-Mediated Phosphine-Aryl Coupling

Chemistry : a European Journal
Charlie BlonsDidier Bourissou

Abstract

The peri-iodo naphthyl phosphine 1 reacts with CuI to give the peri-bridged phosphonio-naphthalene 2, which has been fully characterized (multi-nuclear NMR, MS, XRD). The outcome of the reaction differs markedly from that observed with gold. A two-step pathway involving P-assisted C-I oxidative addition to copper, followed by P-C reductive elimination is shown to be energetically feasible by DFT calculations.

References

Jul 24, 1998·Carbohydrate Research·T AreeH Hoier
Jul 15, 2004·Dalton Transactions : an International Journal of Inorganic Chemistry·James D HoefelmeyerFrançois P Gabbaï
Feb 3, 2005·Journal of the American Chemical Society·Waka NakanishiEiichi Nakamura
Feb 20, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Lei YangRobert P Houser
Mar 29, 2007·The Journal of Physical Chemistry. a·Igor NovakBranka Kovac
Dec 25, 2007·The Journal of Organic Chemistry·David Marcoux, André B Charette
Jul 4, 2008·Journal of the American Chemical Society·Jesse W TyeJohn F Hartwig
Sep 23, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Piotr WawrzyniakPetr Kilian
Feb 3, 2011·Chemistry : a European Journal·Petr KilianJ Derek Woollins
Mar 9, 2011·Journal of the American Chemical Society·Pauline GualcoDidier Bourissou
Feb 22, 2012·Angewandte Chemie·Peter S D RobinsonRichard A J O'Hair
Apr 14, 2012·Nature·Amanda J Hickman, Melanie S Sanford
Apr 3, 2013·Inorganic Chemistry·Sébastien BontempsDidier Bourissou
Aug 27, 2013·Journal of the American Chemical Society·Nicolas LassauqueDidier Bourissou
Jan 18, 2014·Journal of the American Chemical Society·Johannes GuentherDidier Bourissou
Jul 12, 2014·Nature Communications·Marc FontXavi Ribas
Sep 16, 2014·Journal of the American Chemical Society·Andrey I KonovalovVladimir V Grushin
Oct 1, 2014·Journal of the American Chemical Society·Maximilian JoostDidier Bourissou
Oct 30, 2014·Angewandte Chemie·Feriel RekhroukhDidier Bourissou
Mar 3, 2015·Angewandte Chemie·Maximilian JoostDidier Bourissou
Jan 9, 2016·Journal of the American Chemical Society·Hiroyuki KawaiF Dean Toste
Jan 16, 2016·Angewandte Chemie·Maximilian JoostDidier Bourissou
Mar 11, 2017·Chemical Communications : Chem Comm·Shiqing LiJingsong You
Sep 20, 2017·Nature Communications·Abdallah ZeineddineDidier Bourissou
Oct 19, 2017·Chemistry : a European Journal·Xavi Ribas, Marc Devillard

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Citations

Jan 30, 2020·Chemistry : a European Journal·Riccardo BonsignoreAngela Casini
Sep 16, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Maryne DuvalDidier Bourissou
Jan 23, 2019·Journal of the American Chemical Society·Trandon A BenderF Dean Toste

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