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Issue 6, 2017
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3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes

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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.

Graphical abstract: 3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes

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Supplementary files

Article information


Submitted
22 Feb 2017
Accepted
11 Apr 2017
First published
18 Apr 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 4431-4436
Article type
Edge Article

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, 8, 4431
DOI: 10.1039/C7SC00831G

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