Direct Synthesis of Alkenylboronates from Alkenes and Pinacol Diboron via Copper Catalysis

We report an efficient approach for the direct synthesis of alkenylboronates using copper catalysis. The Cu/TEMPO catalyst system (where TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)­oxyl) exhibits both excellent reactivity and selectivity for the synthesis of alkenylboronates, starting from inexpensi...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (1), p.142-146
Main Authors: Lu, Wenkui, Shen, Zengming
Format: Article
Language:English
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Summary:We report an efficient approach for the direct synthesis of alkenylboronates using copper catalysis. The Cu/TEMPO catalyst system (where TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)­oxyl) exhibits both excellent reactivity and selectivity for the synthesis of alkenylboronates, starting from inexpensive and abundant alkenes and pinacol diboron. This approach allows for the direct functionalization of both aromatic and aliphatic terminal alkenes. Mechanistic experiments suggest that the alkenylboronates arise from oxyboration intermediates.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03599