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Rhodium(III)-Catalyzed Cross-Coupling of Alkenylboronic Acids and N-Pivaloyloxylamides

Chao Feng and Teck-Peng Loh*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Email:

C. Feng, T.-P. Loh, Org. Lett., 2014, 16, 3444-3447.

DOI: 10.1021/ol501309e

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A Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides proceeds readily at room temperature and offers a wide functional group tolerance. In combination with hydroboration, this reaction enables a formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.

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ID: J54-Y2014