Potassium organotrifluoroborates

Figure 3.42. Scope of Rh/(if)-binap-catalyzed asymmetric 1,4-addition of potassium organotrifluoroborates to methyl iV-acetamidoacrylate in the presence of guaiacol.

Scheme 9. Proposed mechanism for the Suzuki cross-coupling reaction of arene diazonium salts with potassium organotrifluoroborates based on ESl-MS investigation, m/z vaiues are given for cationic intermediates observed by ESl(+)-MS.

The reaction of aliphatic alcohols and potassium organotrifluoroborate salts also gives ethers. ... 

Tremblay-Morin, J.-P., Raeppel, S., Gaudette, F. Lewis acid-catalyzed Mannich type reactions with potassium organotrifluoroborates. Tetrahedron Lett. 2004, 45, 3471-3474. 

Molander, G. A., Dehmel, F. Formal Total Synthesis of Oximidine II via a Suzuki-Type Cross-Coupling Macrocyclization Employing Potassium Organotrifluoroborates. J. Am. Chem. Soc. 2004, 126, 10313-10318. 

Quach, T. D., Batey, R. A. CopperfllFCatalyzed Ether Synthesis from Aliphatic Alcohols and Potassium Organotrifluoroborate Salts. Org. Lett. 2003, 5,1381-1384. 

Yoshida and coauthors have reported a facile preparation of iodonium salts 367 by the reaction of potassium organotrifluoroborates 366 with (difluoroiodo)arenes under mild conditions (Scheme 2.104) [396]. A similar approach to alkynyliodonium salts by the reaction of alkynyldifluoroboranes with polyfluoroorganyliodine difluorides was developed by Frohn and Bardin [501]. 

These potassium organotrifluoroborates are good partners of S-MC [26]. Coupling of PI1BF3K (20) with deactivated / -bromoanisole proceeds with ligandless Pd catalyst in refluxing MeOH in the presence of K2CO3 [27]. Reaction of more... 

Scheme 4.5). Potassium organotrifluoroborate salts are easily accessible, have attracted increased commercial availability, are air- and moisture-stable alternatives to boronic acids as well as their esters, and can be stored for long periods of time without decomposition under ambient reaction conditions. These aryl donors function brilhantly in arylations of phenols, albeit with the requirement for 2 equiv. of the potassium organotrifluoroborate salt being used to gain the best yields. However, the reactions function even at ambient temperature with molecular oxygen as a co-oxidant [20]. 

A rhodium(l) chloride with chiral diene ligands catalyses addition of potassium organotrifluoroborates (K+ ArBFg") to A-sulfanyl ketimines, effecting C-arylation in good to excellent yields, and ee s up to 99.5%. 0... 

In addition, 2-aminostyrenes have been shown to condense with potassium organotrifluoroborates in the presence of the in situ fluorophile SiCU to give the functionahzed benzo[e][l,2]azaborinines 30 (Scheme 13) (2014JOC365). Sixteen examples of products with this general structure (13—78% yields) were presented. 

The coupling of phenoIs/aUphatic alcohols with potassium organotrifluoroborate could be accomplished using monohydrated Cu(OAc) -DMAP at room tenpraature (Scheme 20.45) [126]. 

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