Chemical Synthesis

Organotrifluoroborates

Potent Boronic Acid Surrogates

In the vast array of catalytic carbon-carbon bond forming reactions, the Suzuki-Miyaura protocol has proven to be a particularly attractive method.  The organoborane nucleophiles (boronic acids, boronate esters, and potassium organotrifluoroborates) readily undergo cross-coupling under mild conditions and in the presence of ordinarily sensitive functional groups (e.g. OH, CO2H, CN, CHO, etc).  However, both boronic acids and boronate esters suffer from limitations.  Boronic acids are difficult to purify and can have uncertain stoichiometry due to trimerization to the corresponding boroxine.  Boronate esters lack atom economy and are more expensive due to the added cost of pinacol or catechol (Figure 1).

Alternatively, potassium organotrifluoroborates:  have known stoichiometry, have a low molecular weight, are insensitive to air and moisture, and are tractable, crystalline solids which are easily stored (Figure 2).1

 

Potassium alkyl-, alkenyl-, aryl-, and heteroaryltrifluoroborates participate in Suzuki-Miyaura cross-coupling reactions yielding versatile synthetic intermediates including:  1,3-dienes, styrenes, sterically hindered biaryls, and highly functionalized heterocyclics (Figure 3).2

In addition to Suzuki-Miyaura coupling, potassium organotrifluoroborates participate in a variety of other useful reactions including:  1,2- and 1,4-addition, C—O and C—N bond formation, and halogenation, and allylation (Figure 4).3



   Product Information


Prod. No. Product Name Structure Add to Cart
637890 Potassium methyltrifluoroborate
659274 Potassium allyltrifluoroborate, 95%
660094 Potassium butyltrifluoroborate, 95%
563056 Potassium benzyltrifluoroborate, 95%
563099 Potassium phenethyltrifluoroborate, 95%
655228 Potassium vinyltrifluoroborate, 95%
637882 Potassium trans-1-decenyltrifluoroborate, 95%
576158 Potassium trans-styryltrifluoroborate
563951 Potassium phenyltrifluoroborate, 95%
571547 Potassium 4-bromophenyltrifluoroborate
571555 Potassium p-tolyltrifluoroborate
571563 Potassium 3,5-bis(trifluoromethyl)-phenyltrifluoroborate
571598 Potassium 3-nitrophenyltrifluoroborate
576093 Potassium 4-formylphenyltrifluoroborate
576107 Potassium 2-bromophenyltrifluoroborate, 96%
576115 Potassium 3-methoxyphenyltrifluoroborate, 96%
576123 Potassium o-tolyltrifluoroborate
576131 Potassium 4-(trifluoromethyl)-phenyltrifluoroborate, 96%
579068 Potassium 4-methoxyphenyltrifluoroborate, 95%
592846 Potassium 4-fluorophenyltrifluoroborate, 95%
592943 Potassium 2,6-dimethylphenyltrifluoroborate, 95%
597929 Potassium 2,6-difluorophenyltrifluoroborate
654728 Potassium 4-tert-butylphenyltrifluoroborate, 95%
654930 Potassium 2-methoxyphenyltrifluoroborate, 95%
656992 Potassium 2,4-difluorophenyltrifluoroborate, 95%
657018 Potassium 2-naphthalenetrifluoroborate
657050 Potassium 4-acetylphenyltrifluoroborate, 97%
657069 Potassium 4-carboxyphenyltrifluoroborate, 97%
657077 Potassium 4-chlorophenyltrifluoroborate, 95%
657085 Potassium 2,6-dimethoxyphenyltrifluoroborate, 95%
657093 Potassium 3-formylphenyltrifluoroborate, 95%
657115 Potassium 4-(methylthio)-phenyltrifluoroborate, 95%
659746 Potassium 3-hydroxyphenyltrifluoroborate, 96%
659762 Potassium 4-(hydroxymethyl)-phenyltrifluoroborate
659770 Potassium 3-fluorophenyltrifluoroborate, 96%
659789 Potassium 3-carboxyphenyltrifluoroborate, 97%
659754 Potassium 3,4-(methylenedioxy)-phenyltrifluoroborate
571571 Potassium 3-thiophenetrifluoroborate
654949 Potassium 5-methyl-2-thiophenetrifluoroborate, 95%

CheminarTM 1.2 Potassium Organotrifluoroborates: High-Performance Boronic Acid/Ester Surrogates

References:

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    (b) Genêt, J.-P.; Darses, S. Eur. J. Org. Chem. 2003, 4313-4327.

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  3. (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683-1686;
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    (i) Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 7, 990-998;
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    (k) Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827-3830;
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