Suzuki reaction heteroaromatic compounds

The aforementioned PEPPSI-IPr pre-catalyst 16 has also been used in the Suzuki-Miyaura reaction. This pre-catalyst allowed the easy preparation of hindered biaryls and drug-like heteroaromatic compounds in good to excellent yields (Scheme 6.27). 

Bis-indole alkaloids, such as 208, possess interesting scaffolds with biological activity. A general route to these compounds that allowed for various heteroaromatic rings to be used as the linker for the indole moieties was desired and the Suzuki reaction of 206 with 207 appeared to be the most direct method for their assembly [74]. 

Satoh, M. Miyaura, N. Suzuki, A. 1987. Palladium catalyzed cross-coupling reaction of (1-ethoxy-l-alken-2-yl)boranes with ortho-functionalized iodoarenes. A novel and convenient synthesis of benzo fused heteroaromatic compounds. Synthesis 373-377. 

The Suzuki coupling reaction is a powerful tool for the construction of biaryl compounds and their homologues, which are key structural elements of various natural products, polymers, and compounds of medicinal interest. Aryl boronic acids and their esters are the usual substrates in reactions with aryl or heteroaromatic halides and... 

A ramification of the DreM strategy in an unusual heteroaromatic framework is illustrated in the synthesis of the previously unknown triazadibenzo[cd,/]azulen-7(6H)-one 75 in which the imidazopyridines 70 and 71 are coupled by a Suzuki-Miyaura reaction with the DoM-derived boronic add 72 to give 73 and 74, respectively (Scheme 14.18). Compound 74 undergoes DreM cyclization on treatment with LiTMP to give the potentially bioactive 75 in modest yields [126]. 

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