Pham MV, Cramer N * École Polytechnique Fédérale de Lausanne, Switzerland
Aromatic Homologation by Non-Chelate-Assisted Rh
III-Catalyzed C–H Functionalization of Arenes with Alkynes.
Angew. Chem. Int. Ed. 2014;
53: 3484-3487
Key words
polyaromatic hydrocarbons - rhodium - C–H functionalization
Significance
Extending the conjugation length of arenes is of great interest to the materials chemistry
community due to the impartation of new electrical and photophysical properties. The
previously reported method for rhodium-catalyzed arene homologation was achieved
with a boronic acid functionalized substrates (J. Org. Chem. 2011, 76, 2867); in contrast, Pham and Cramer report a C–H functionalization to achieve the
same transformation.
Comment
While dibutyl alkynes were used most prominently in this paper, the authors were also
able to demonstrate that other alkynes, including those bearing aryl groups, could
be incorporated. A proposed mechanism for the transformation is included in the paper.