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.
Highlights
The Suzuki–Miyaura cross-coupling is one of the most often utilized reactions in the synthesis of pharmaceutical compounds and conjugated materials
The Suzuki–Miyaura cross-coupling, in which organoboranes are coupled with organic halides or their equivalents (Fig. 1a), has changed the way organic molecules are assembled[1,2]. This reaction is the method of choice for the preparation of biaryl or polyene units in pharmaceutical[3] and materials industries[4]
Because of the ease with which biaryl molecules are prepared using the Suzuki–Miyaura reaction, these substructures are widely found in pharmaceutical products and precursors, perhaps even to the detriment of structural diversity
Summary
The Suzuki–Miyaura cross-coupling is one of the most often utilized reactions in the synthesis of pharmaceutical compounds and conjugated materials. In 2009, we reported the first example of the cross-coupling of chiral benzylic boronic esters (1) that occurred with retention of stereochemistry (Fig. 2)[9].
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