|
|
|
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:
- For recent reviews, see:
(a) Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49-56;
(b) Genêt, J.-P.; Darses, S. Eur. J. Org. Chem. 2003, 4313-4327.
- (a) Molander, G. A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148-11149;
(b) Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393-396;
(c) Molander, G. A.; Yun, C-S.; Ribagorda, M.; Biolatto, B. J. Org. Chem. 2003, 68, 5534-5539;
(d) Fang, G.-H.; Yan, Z.-J.; Deng, M-H. Org. Lett. 2004, 6, 357-360;
(e) Charette, A. B.; Mathieu, S.; Fournier, J.-F. Synlett 2005, 11, 1779-1782;
(f) Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3950-3956;
(g) Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107-109;
(h) Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424-8429;
(i) Molander, G. A.; Katona, B. W.; Machrouhi, F. J. Org. Chem. 2002, 67, 8416-8423;
(j) Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867-1870;
(k) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302-4314;
(l) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649-2652;
(m) Kabalka, G. W.; Al-Masum, M. Tetrahedron Lett. 2005, 46, 6329-6331.
- (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683-1686;
(b) Bolshan, Y.; Batey, R. A. Org. Lett. 2005, 7, 1481-1484;
(c) Pucheault, M.; Darses, S.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 6155-6157;
(d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552-3557;
(e) Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045-8052;
(f) Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69-73;
(g) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381-1384;
(h) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397-4400;
(i) Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 7, 990-998;
(j) Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289-4292;
(k) Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827-3830;
(l) Solin, N.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2005, 7, 689-691;
(m) Kabalka, G. W.; Venkataiah, B.; Dong, G. Org. Lett. 2003, 5, 3803-3805;
(n) Kabalka, G. W.; Mereddy, A. R. Organometallics 2004, 23, 4519-4521;
(o) Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 343-345;
(p) Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 1417-1419.
|
|
