Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols

Núria Miralles; Rauful Alam; Kálmán J Szabó; Elena Fernández

doi:10.1002/anie.201511255

Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols

Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4303-7. doi: 10.1002/anie.201511255. Epub 2016 Mar 2.

Authors

Núria Miralles¹, Rauful Alam², Kálmán J Szabó², Elena Fernández³

Affiliations

¹ Department Química Física i Inorgànica, University Rovira i Virgili, C/Marcel⋅lí Domingo s/n, Tarragona, Spain.
² Department of Organic Chemistry, Stockholm University, Sweden.
³ Department Química Física i Inorgànica, University Rovira i Virgili, C/Marcel⋅lí Domingo s/n, Tarragona, Spain. mariaelena.fernandez@urv.cat.

Abstract

The base-catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1-disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid-base adduct, [Hbase](+) [MeO-B2 pin2 ](-) favored the formation of 1,2,3-triborylated species from the tertiary allylic alcohols and 1-propargylic cyclohexanol at 90 °C.

Keywords: allyl boronates; allylic alcohols; allylic borylation; metal-free; polyboronates.

Publication types

Research Support, Non-U.S. Gov't