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Facile Phenylphosphinidene Transfer Reactions from Carbene–Phosphinidene Zinc Complexes
Author(s) -
Krachko Tetiana,
Bispinghoff Mark,
Tondreau Aaron M.,
Stein Daniel,
Baker Matthew,
Ehlers Andreas W.,
Slootweg J. Chris,
Grützmacher Hansjörg
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703672
Subject(s) - carbene , phosphinidene , chemistry , reactivity (psychology) , adduct , phosphine , moiety , lewis acids and bases , zinc , phosphorus , singlet state , combinatorial chemistry , substrate (aquarium) , photochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , physics , pathology , nuclear physics , excited state , oceanography , geology , alternative medicine
Phosphinidenes [R‐P] are convenient P 1 building blocks for the synthesis of a plethora of organophosphorus compounds. Thus far, transition‐metal‐complexed phosphinidenes have been used for their singlet ground‐state reactivity to promote selective addition and insertion reactions. One disadvantage of this approach is that after transfer of the P 1 moiety to the substrate, a challenging demetallation step is required to provide the free phosphine. We report a simple method that enables the Lewis acid promoted transfer of phenylphosphinidene, [PhP], from NHC=PPh adducts (NHC=N‐heterocyclic carbene) to various substrates to produce directly uncoordinated phosphorus heterocycles that are difficult to obtain otherwise.