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Iterative protecting group-free cross-coupling leading to chiral multiply arylated structures

C. Crudden,Christopher Ziebenhaus,Jason P. G. Rygus,Kazem Ghozati,Phillip J. Unsworth,Masakazu Nambo,Samantha Voth,M. Hutchinson,Veronique S. Laberge,Yuuki Maekawa,Daisuke Imao

Published 2016 in Nature Communications

ABSTRACT

The Suzuki–Miyaura cross-coupling is one of the most often utilized reactions in the synthesis of pharmaceutical compounds and conjugated materials. In its most common form, the reaction joins two sp2-functionalized carbon atoms to make a biaryl or diene/polyene unit. These substructures are widely found in natural products and small molecules and thus the Suzuki–Miyaura cross-coupling has been proposed as the key reaction for the automated assembly of such molecules, using protecting group chemistry to affect iterative coupling. We present herein, a significant advance in this approach, in which multiply functionalized cross-coupling partners can be employed in iterative coupling without the use of protecting groups. To accomplish this, the orthogonal reactivity of different boron substituents towards the boron-to-palladium transmetalation reaction is exploited. The approach is illustrated in the preparation of chiral enantioenriched compounds, which are known to be privileged structures in active pharmaceutical compounds. The Suzuki-Miyaura cross coupling is widely used in industrial and academic settings for the formation of carbon-carbon bonds. Here, the authors report a procedure whereby a molecule with multiple reactive carbon-boron bonds can undergo sequential, selective Suzuki-Miyaura reactions without the need for protecting groups.

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