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3-Cyanoallyl Boronates Are Versatile Building Blocks in the Synthesis of Polysubstituted Thiophenes

Abstract

We report the preparation of hitherto unprecedented 3-cyanoallyl boronates using condensation of the parent α-boryl aldehyde and nitriles. The resulting allyl boronates have been used to generate a wide range of borylated thiophenes, which represent a valuable class of heterocycles in modern drug discovery. Subsequent Suzuki-Miyaura cross-coupling enabled the synthesis of pharmaceutically important 3,5-disubstituted aminothiophenes. Moreover, late stage functionalization gave access to borylated bromothiophene and thieno[2,3-b]pyridines.

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Publication details

The article was received on 22 Feb 2017, accepted on 11 Apr 2017 and first published on 18 Apr 2017


Article type: Edge Article
DOI: 10.1039/C7SC00831G
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
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    3-Cyanoallyl Boronates Are Versatile Building Blocks in the Synthesis of Polysubstituted Thiophenes

    W. Shao, S. J. Kaldas and A. K. Yudin, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC00831G

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