Potassium Vinyltrifluoroborate as a Versatile Dianion Precursor

By: Aaron Thornton, Chemfiles Volume 11 Article 1

Molander and co-workers have developed a powerful strategy for the production of a unique 1,2-dianion equivalent using potassium vinyltrifluoroborate.1 This useful organotrifluoroborate undergoes selective hydroboration with 9-BBN to generate (3), a 1,2-dianion equivalent that can then undergo a variety of selective transformations (Scheme 1).

Scheme 1: Hydroborated intermediate (3) as a 1,2-dianion equivalent.(655228)

This versatile 1,2-dianion equivalent undergoes sequential Suzuki-Miyaura cross-coupling with a range of organic electrophiles, including aryl-, heteroaryl-, and alkenyl halides (Table 1).

Table 1: Sequential Suzuki-Miyaura cross-couplings to build molecular complexity from potassium vinyltrifluoroborate.

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  1. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275.
  2. Molander. G. A.; Sandrock, D. L. Org. Lett. 2009, 11, 2369.

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