Premium
3‐Bromo‐2‐Pyrone: An Alternative and Convenient Route to Functionalized Phosphinines
Author(s) -
Habicht Marija H.,
Wossidlo Friedrich,
Weber Manuela,
Müller Christian
Publication year - 2016
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.201602012
Subject(s) - pyrone , combinatorial chemistry , chemistry , stereochemistry
The facile access to 3‐bromo‐2‐pyrone allows the preparation of 6‐bromo‐2‐trimethylsilyl‐phosphinine by a [4+2] cycloaddition with Me 3 Si‐C≡P for the first time. The regioselectivity of this reaction could be verified by means of single crystal X‐ray diffraction of the corresponding W 0 complex. In the presence of ZnBr 2 and dppp (1,3‐bis(diphenylphosphino)propane) as a bidentate ligand, the bromo‐phosphinine quantitatively undergoes a Negishi cross‐coupling reaction with PhLi that selectively leads to 6‐phenyl‐2‐trimethylsilyl‐phosphinine. This heterocycle could again be characterized by means of X‐ray diffraction as a W 0 complex. These results describe a new and convenient route to 2,6‐disubstituted phosphinines that makes use of readily available starting materials.