Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5223765 | Tetrahedron | 2008 | 12 Pages |
Abstract
Iridium-catalyzed borylation has been applied to various substituted thiophenes to synthesize poly-functionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe) and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3- and 2,5-di-substituted thiophenes. Electrophilic aromatic C-H/C-Si bromination on thiophene boronate esters is shown to take place without breaking the C-B bond, and one-pot C-H borylation/Suzuki-Miyaura cross-coupling has been accomplished on 2- and 3-borylated thiophenes.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Ghayoor A. Chotana, Venkata A. Kallepalli, Robert E. Jr., Milton R. III,