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Borophosphonate Cages: Easily Accessible and Constitutionally Dynamic Heterocubane Scaffolds
Author(s) -
Tönnemann Justus,
Scopelliti Rosario,
Zhurov Konstantin O.,
Menin Laure,
Dehnen Stefanie,
Severin Kay
Publication year - 2012
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.201201287
Subject(s) - bent molecular geometry , toluene , scrambling , condensation , chemistry , covalent bond , dynamic covalent chemistry , nanotechnology , combinatorial chemistry , crystallography , materials science , organic chemistry , crystal structure , computer science , physics , thermodynamics , supramolecular chemistry , algorithm
Abstract A versatile and experimentally facile procedure for the synthesis of borophosphonate cages of the general formula [ t BuPO 3 BR′] 4 is described. The method involves heating of tert ‐butylphosphonic acid with a boronic acid in toluene to give borophosphonates in [4+4] condensation reactions. The products display a heterocubane structure with bent P‐O‐B bridges as evidenced by crystallographic analyses. Scrambling experiments show that the borophosphonate cages are constitutionally dynamic scaffolds with exchange reactions occurring on the hour time scale at room temperature. The cages can be decorated with reactive groups such as aldehydes. Our results demonstrate that borophosphonate cages are interesting building blocks for dynamic covalent chemistry.