Enabling the direct synthesis of multi-functionalized iodoarenes as accessible sophisticated building blocks for sustainable catalytic sequences

In the last 20-years, palladium-catalyzed C–H activation has emerged as a useful alternative to traditional cross-coupling methods and a powerful tool to access valuable intermediates for the synthesis of complex functional molecules.

The biaryl fragment is one of the most frequent units present in bioactive molecules, functional organic materials and natural products.

Despite major advances, significant limitations persist with regard to their preparation, in term of reactivity, selectivity and sustainability.

Based on the recent achievements in the synthesis of ortho-iodobiaryls following a Catellani strategy, the overall objective of this proposal is the development of a general and sustainable method for the direct synthesis of ortho-iodobiaryls and selectively substituted haloarenes as valuable intermediates for the synthesis of a large number of high value-added compounds.

The project aims also to develop protocols for the straightforward synthesis of new biaryl-containing phosphines, as a valuable application of this methodology.

CAT4Arene will allow the selective construction of halogenated biaryls and arenes which can be further easily converted into a broad variety of high value-added compounds.

In particular, thanks to the easily manipulation of the C-halogen bond, especially C-I and C-Br bonds, these new methodologies will unlock the direct construction of tricky molecular architectures, including biaryl-containing phosphines and bioactive nitrogen derivatives.

Likewise, new classes of organic molecules would be also accessed, unlocking the opportunity to enlarge the range of compounds available for the medicinal chemistry and the agrochemical industry.

The development of unconventional haloarenes formation protocols will be an outstanding breakthrough for the organic chemistry community.