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Aryltrifluoroborate salts are more nucleophilic than the corresponding arylboronic acids and undergo ligand-free Pd-catalyzed cross-coupling reactions with arenediazonium tetrafluoroborates to give good yields of biaryls. Suzuki Cross-Coupling are conducted using organotrifluoroborates as a potent boronic acid surrogates. In the presence of Dicarbonyl(2,4-pentanedionato)rhodium(I), 39295, K aryl- and alkenyltrifluoroborates add to aldehydes and enones to give secondary alcohols and saturated ketones, respectively.
Alexander K.L. Yuen.; Craig A. Hutton. Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates.Tetrahedron Lett. 2005, 46 (46),7899-7903 .
George W. Kabalk.; Mohammad Al-Masum. Microwave enhanced cross-coupling reactions involving potassium organotrifluoroborates.Tetrahedron Lett. 2005, 46 (37),6329-6331 .
Treatment with TMS chloride in acetonitrile generates the Lewis acid phenylboron difluoride in situ, avoiding the need to handle boron trihalides: J. Org. Chem., 60, 3020 (1995).
Aryltrifluoroborate salts are more nucleophilic than the corresponding arylboronic acids and undergo ligand-free Pd-catalyzed cross-coupling reactions with arenediazonium tetrafluoroborates to give good yields of biaryls: Tetrahedron Lett., 38, 4393 (1997); Eur. J. Org. Chem., 1875 (1999). Cross-coupling with aryl or heteroaryl halides and triflates, under ligand-free conditions, has subsequently been reported: Org. Lett., 4, 1867 (2002).
Coupling with diaryliodonium salts has also been reported: Synth. Commun., 29, 2457 (1999). The method has been extended to the synthesis of benzophenones by carbonylative cross-coupling in the presence of CO: J. Chem. Res. (Synop.), 400 (1999).
In the presence of Dicarbonyl(2,4-pentanedionato)rhodium(I), 39295, K aryl- and alkenyltrifluoroborates add to aldehydes and enones to give secondary alcohols and saturated ketones, respectively: Org. Lett., 1, 1683 (1999):
Asymmetric Rh-catalyzed additions to enones in the presence of a chiral BINAP catalyst give the corresponding saturated ketones in high yield and ee: Eur. J. Org. Chem., 3552 (2002).
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