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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.

SUBMITTER: Shao W

PROVIDER: S-EPMC5590094 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes.

Shao Wenjie W Kaldas Sherif J SJ Yudin Andrei K AK

Chemical science 20170418 6

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 ...[more]

PMID: 28936329

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