SYNLETT Best Paper Award 2017: Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes

Cathleen Crudden and Masakazu Nambo highlight their award-winning paper on an elegant synthesis of tetraarylmethanes.

The award-winning article deals with the synthesis of tetraarylmethanes. Polyarylated methanes are valuable structures found in a variety of biologically active molecules and functional organic materials. Among arylated methanes, fully- or tetra-arylated methanes are structurally beautiful molecules that have unique chemical and physical properties and are challenging to prepare. This rigid motif has been used as a ligand for metal–organic frameworks, n-type material for optoelectronic devices, and an agent for drug delivery. Very bulky tetraarylmethanes are also critical as ‘stoppers’ in rotaxane chemistry, subject of the Nobel Prize in 2016. Despite intense interest in tetraarylmethanes for these applications, most synthetic approaches rely on very classical methods, such that finding modular and straightforward syntheses of unsymmetrical tetraarylmethanes is still a challenge in synthetic organic chemistry. In this paper, the authors have established a new synthetic route for the preparation of tetraarylmethanes from triarylmethanes and arenes by a formal cross-dehydrogenative coupling.


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