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Formation of a peri ‐Bridged Phosphonio‐Naphthalene by Cu‐Mediated Phosphine–Aryl Coupling
Author(s) -
Blons Charlie,
Duval Maryne,
Delcroix Damien,
OlivierBourbigou Hélène,
MalletLadeira Sonia,
Sosa Carrizo E. Daiann,
Miqueu Karinne,
Amgoune Abderrahmane,
Bourissou Didier
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802579
Subject(s) - naphthalene , phosphine , chemistry , aryl , peri , reductive elimination , copper , medicinal chemistry , oxidative addition , oxidative coupling of methane , stereochemistry , organic chemistry , catalysis , philosophy , alkyl , theology
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.