Download PDF
Synfacts 2011(6): 0615-0615  
DOI: 10.1055/s-0030-1260411
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

9-H-9-Borafluorene: Hydroboration and Oligomerization

Contributor(s): Timothy M. Swager, Olesya Haze
A. Hübner, Z.-W. Qu, U. Englert, M. Bolte, H.-W. Lerner, M. C. Holthausen*, M. Wagner*
Johann Wolfgang Goethe-Universität Frankfurt and RWTH Aachen, Germany
Further Information

Publication History

Publication Date:
19 May 2011 (online)

    Permissions and Reprints

Significance

The elusive 9-H-9-borafluorene was generated in situ via Br-H exchange between 9-Br-9-borafluorene 1 and triethylsilane. At room temperature, NMR observations point to the formation of a non-classical dimer 2. This can undergo further reaction with pyridine to form the known adduct 3 in quantitative yield. Addition of a terminal alkyne to the solution of 2 led to the hydroboration products 4 and 5. When the reaction mixture is heated a different dimer (6) is produced.