Synlett 2016; 27(11): 1674-1676
DOI: 10.1055/s-0035-1561944
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Stabilities of 3-Borylated Indoles

Muhannad A. E. Al-Saedy
Department of Chemistry, The University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK   eMail: j.harrity@sheffield.ac.uk
,
Joseph P. A. Harrity*
Department of Chemistry, The University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK   eMail: j.harrity@sheffield.ac.uk
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Publikationsverlauf

Received: 10. Februar 2016

Accepted after revision: 03. März 2016

Publikationsdatum:
18. März 2016 (online)


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Abstract

We report herein that 3-pinacol boronic esters undergo facile protodeborylation in the presence of palladium catalysts and base, and this contributes significantly to the generation of nonborylated indole byproducts in the B2Pin2-mediated palladium-catalysed borylative cyclization of 2-alkynylanilides. Suginome’s reagent provides an alternative method to access 3-borylated indoles as these compounds are less susceptible to protodeborylation.

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