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. 2006 May 11;8(10):2031-4.
doi: 10.1021/ol060375a.

Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates

Gary A Molander  1 , Jungyeob Ham
Affiliations

Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates

Gary A Molander et al. Org Lett. .

Abstract

[reaction: see text] Potassium bromo- and iodomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF(2). Moreover, a new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of the halide in these potassium halomethyltrifluoroborates is described.

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Figures

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(3)
Figure 1
Figure 1
Reaction mechanism of the nucleophilic displacement of α-halo boronate esters with various nucleophiles and the one-carbon homologation of boronate esters with (dihalomethyl)lithium.
See this image and copyright information in PMC

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